| Identification | More | [Name]
BOC-GLY-OSU | [CAS]
3392-07-2 | [Synonyms]
BOC-GLYCINE 4-HYDROXYSUCCINIMIDE ESTER
BOC-GLYCINE HYDROXYSUCCINIMIDE ESTER
BOC-GLYCINE N-HYDROXYSUCCINIMIDE ESTER
BOC-GLYCINE-OSU
BOC-GLY-OSU
N-ALPHA-T-BOC-GLYCINE N-HYDROXYSUCCINIMIDE ESTER
tert-butyl [2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl]carbamate
Boc-L-Glycine 4-Hydroxysuccinimide Ester
N-alpha-t-Butyloxycarbonyl-glycine succinimidyl ester
BOC-GLYCINE-HYDROXYSUCCINIMIDESTER
BOC-L-GLYCINEN-HYDROXYSUCCINIMIDEESTER
[(tert-Butoxycarbonyl)amino]acetic acid succinimidyl ester
[2-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl]carbamic acid 1,1-dimethylethyl ester
N-(tert-Butoxycarbonyl)glycine succinimidyl ester
N-(tert-Butyloxycarbonyl)glycine 2,5-dioxo-1-pyrrolidinyl ester
N-[[N-(tert-Butoxycarbonyl)glycyl]oxy]succinimide | [EINECS(EC#)]
222-230-2 | [Molecular Formula]
C11H16N2O6 | [MDL Number]
MFCD00042761 | [Molecular Weight]
272.25 | [MOL File]
3392-07-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
165-167 °C | [density ]
1.31±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
10.51±0.46(Predicted) | [color ]
White | [Sensitive ]
Hygroscopic | [BRN ]
1549242 | [CAS DataBase Reference]
3392-07-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white powder | [Uses]
peptide synthesis | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
Step 2: Synthesis of 2,5-dioxopyrrolidin-1-yl 2-(tert-butoxycarbonylamino) acetate. N-Boc-glycine (7.31 g, 41.7 mmol) was dissolved in 100 mL of dichloromethane (DCM) and the solution was cooled to 15 °C. Subsequently, N-hydroxysuccinimide (5.28 g, 45.9 mmol) was added to the cooled solution. Under vigorous stirring, N,N'-dicyclohexylcarbodiimide (9.47 g, 45.9 mmol) was added to the formed suspension. The reaction mixture transformed into a cloudy white suspension within seconds. The reaction mixture was gradually warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the insoluble by-products were removed by filtration through diatomaceous earth, the filtrate was washed with 50 mL of saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and finally concentrated under vacuum to give the product as a white crystalline powder. Yield: 7.02 g, yield 61.8%. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 1.38 (s, 9H), 2.80 (s, 4H), 4.07 (d, J = 6 Hz, 2H), 7.43 (br s, 1H). Mass spectrum (ESI) m/z 567.2 [2M + Na]+. | [References]
[1] Chemistry - A European Journal, 2016, vol. 22, # 52, p. 18865 - 18872
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 15, p. 2443 - 2449
[3] Chemical communications (Cambridge, England), 2003, # 23, p. 2870 - 2871
[4] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 4, p. 402 - 407
[5] Helvetica Chimica Acta, 2004, vol. 87, # 5, p. 1077 - 1089 |
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