| Identification | Back Directory | [Name]
BOC-D-DAP-OH | [CAS]
76387-70-7 | [Synonyms]
BOC-D-DAP-OH
BOC-D-DAPA-OH
3-AMino-N-Boc-D-alanine
N-t-BOC-?amino-D-alanine
N-Boc-beta-Amino-D-alanine
N-T-BOC-BETA-AMINO-D-ALANINE
(Tert-Butoxy)Carbonyl D-Dap-OH
BOC-D-2,3-DIAMINOPROPIONIC ACI
BOC-D-2,3-DIAMINOPROPIONIC ACID
N-TERT-BOC-BETA-AMINO-D-ALANINE
N2-BOC-R-2,3-DIAMINOPROPIONIC ACID
N-α-Boc-D-2,3-diaminopropionic acid
N-ALPHA-BOC-D-DIAMINOPROPIONIC ACID
N-A -BOC-D-2,3-DIAMINOPROPIONIC ACID
Na-Boc-(R)-2,3-diaminopropionic acid
BOC-D-ALPHA,BETA-DIAMINOPROPIONIC ACID
N-ALPHA-BOC-D-2,3-DIAMINOPROPIONIC ACID
N(^a)-Boc-D-2,3-diaminopropionicacid,97%
3-Amino-N-(tert-butoxycarbonyl)-D-alanine
N-ALPHA-BOC-(R)-2,3-DIAMINOPROPIONIC ACID
a-N-tert-butoxycarbonyl-b-amino-L-alanine
Nα-Boc-D-2,3-diaMinopropionic acid
Boc-D-Dap-OH(Na-Boc-D-2,3-DiaMinopropionic acid)
Nα-Boc-D-2,3-diaminopropionic acid≥ 99% (Titration)
D-Alanine,3-aMino-N-[(1,1-diMethylethoxy)carbonyl]-
N-ALPHA-T-BUTOXYCARBONYL-D-2,3-DIAMINOPROPIONIC ACID
(R)-2-(Aminomethyl)-4-(tert-butoxy)-4-oxobutanoicacid
N-ALPHA-T-BUTYLOXYCARBONYL-D-2,3-DIAMINOPROPIONIC ACID
(R)-3-AMino-2-((tert-butoxycarbonyl)aMino)propanoic acid
N-ALPHA-TERT-BUTYLOXYCARBONYL-D-2,3-DIAMINOPROPIONIC ACID
(2R)-3-amino-2-{[(tert-butoxy)carbonyl]amino}propanoic acid
(2R)-3-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoicacid | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C8H16N2O4 | [MDL Number]
MFCD01632072 | [MOL File]
76387-70-7.mol | [Molecular Weight]
204.22 |
| Chemical Properties | Back Directory | [Melting point ]
200-203℃ | [Boiling point ]
364.4±37.0 °C(Predicted) | [density ]
1.189±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT. | [form ]
solid | [pka]
2.88±0.16(Predicted) | [color ]
White | [Optical Rotation]
Consistent with structure | [InChI]
InChI=1S/C8H16N2O4/c1-8(2,3)14-7(13)10-5(4-9)6(11)12/h5H,4,9H2,1-3H3,(H,10,13)(H,11,12)/t5-/m1/s1 | [InChIKey]
KRJLRVZLNABMAT-RXMQYKEDSA-N | [SMILES]
C(O)(=O)[C@@H](CN)NC(OC(C)(C)C)=O |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white powder | [Uses]
N(alpha)-Boc-D-2,3-diaminopropionic acid is used as pharmaceutical intermediate. | [Synthesis]
N-Boc-L-asparagine (13; 3.48 g, 15 mmol) was used as starting material, which was co-dissolved with PIDA (5.81 g, 18 mmol) in a solvent mixture of EtOAc, MeCN, and H2O (2:2:1, v/v, total volume 62.5 mL). The reaction was carried out at 16°C for 30 min. Subsequently, the reaction system was slowly warmed to room temperature and stirring was continued for 4 hours. A precipitate was generated during the reaction, which was collected by filtration and dried to afford the target product (R)-3-amino-2-((tert-butoxycarbonyl)amino)propionic acid in a yield of 2.02 g (66% yield, 9.89 mmol) as a colorless solid with a melting point of 211-213 °C (literature value 216 °C). The product was confirmed by 1H NMR (500 MHz, DMSO-d6): δ= 1.40 [s, 9H, C(CH3)3], 2.76 (dd, 3J = 9.2 Hz, 2J = 11.8 Hz, 1H, CH2), 3.06 (dd, 3J = 5.1 Hz, 2J = 11.8 Hz, 1H, CH2), 3.65-3.69 (m 1H, COCH), 6.08 (s, 1H, OCONH). No proton signals were observed for the COOH and NH2 groups.13C NMR (125 MHz, DMSO-d6) data: δ = 28.3, 40.8, 51.1, 78.2, 155.2, 171.2. LC-MS (ESI) analysis showed 100% purity of the product; m/z = 205.19 ([M + H]+), 203.09 ([ M - H]-). HRMS (ESI+) analysis results: calculated value C8H16N2O4 ([M + H]+) m/z = 205.1183; measured value: 205.1177. | [References]
[1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 6, p. 1629 - 1633
[2] Chemical Communications, 2011, vol. 47, # 4, p. 1198 - 1200
[3] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5696 - 5704
[4] Synlett, 2008, # 4, p. 513 - 516
[5] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214 |
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