| Identification | More | [Name]
Ethyl L-pyroglutamate | [CAS]
7149-65-7 | [Synonyms]
5-OXO-PROLINE ETHYL ESTER
ETHYL L-PYROGLUTAMATE
ETHYL (S)-2-PYRROLIDINONE-5-CARBOXYLATE
ETHYL (S)-(+)-2-PYRROLIDONE-5-CARBOXYLATE
ETHYL (S)-2-PYRROLIDONE-5-CARBOXYLATE
ETHYL (S)-PYROGLUTAMATE
H-PYR-OET
(+)-L-PYROGLUTAMIC ACID ETHYL ESTER
L-PYROGLUTAMIC ACID ETHYL ESTER
PYR-OET
(S)-5-OXOPROLINE ETHYL ESTER
(S)-ETHYL 2-PYRROLIDONE-5-CARBOXYLATE
SPECS AQ-405/40679537
ethyl 5-oxo-L-prolinate
(S)-(+)-5-Ethylcarboxyl-2-pyrrolidinone
5-Oxo-L-proline Ethyl Ester
Ethyl (2S)-5-Oxopyrrolidine-2-carboxylate
NSC 166529
NSC 7227
ETHYL(S)-(-)-2-PYRROLIDINE-5-CARBOXYLATE | [EINECS(EC#)]
230-480-9 | [Molecular Formula]
C7H11NO3 | [MDL Number]
MFCD00064497 | [Molecular Weight]
157.17 | [MOL File]
7149-65-7.mol |
| Chemical Properties | Back Directory | [Appearance]
White to cream low melting solid | [Melting point ]
54-56 °C
| [alpha ]
-3.5 º (c=5, water) | [Boiling point ]
176 °C12 mm Hg(lit.)
| [density ]
1.2483 (rough estimate) | [refractive index ]
1.4310 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
0-6°C | [form ]
Low Melting Solid | [pka]
14.78±0.40(Predicted) | [color ]
White to cream | [Optical Rotation]
[α]19/D +3.3°, c = 10 in ethanol | [BRN ]
82621 | [InChI]
InChI=1S/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m0/s1 | [InChIKey]
QYJOOVQLTTVTJY-YFKPBYRVSA-N | [SMILES]
C(OCC)(=O)[C@@H]1CCC(=O)N1 | [LogP]
-1.390 (est) | [CAS DataBase Reference]
7149-65-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [F ]
3-10 | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
White to cream low melting solid | [Uses]
(S)-(+)-5-Ethylcarboxyl-2-pyrrolidinone (cas# 7149-65-7) is a compound useful in organic synthesis. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
30.0 g (232 mmol) of L-pyroglutamic acid was suspended in 100 mL of anhydrous ethanol and 20 mL (274 mmol, 1.2 eq.) of SOCl2 was slowly added dropwise at 0 °C. After the dropwise addition, the reaction mixture was stirred at 0 °C for 15 h. The reaction mixture was then allowed to warm up naturally to room temperature, resulting in a clarified solution. After completion of the reaction, all volatile components were removed under reduced pressure. The residue was dissolved in 500 mL of ethyl acetate and treated sequentially with K2CO3 and MgSO4 with stirring, removing the desiccant by filtration after each treatment. The solution was filtered through a small amount of silica gel and concentrated under reduced pressure to give 36.0 g (230 mmol, 99% yield) of the target product, ethyl (S)-5-oxopyrrolidine-2-carboxylate, in the form of a yellowish viscous oil. 2.22-2.48 (m, 3H, H-3α, H-4), 2.07-2.22 (m, 1H, H-3β), 1.22 (t, 3H, J = 7.1 Hz, ester CH3).13C-NMR (75 MHz, CDCl3): δ (ppm) = 178.37 (lactam CO), 172.10 (ester CO), 61.58 ( ester CH2), 55.59 (CH), 29.33 (CH2, C-4), 24.77 (CH2, C-3), 14.11 (ester CH3). | [References]
[1] Angewandte Chemie - International Edition, 2010, vol. 49, # 39, p. 7111 - 7115
[2] Patent: US2011/34438, 2011, A1. Location in patent: Page/Page column 20
[3] Patent: CN107304179, 2017, A. Location in patent: Paragraph 0033-0034
[4] Chemical Communications, 2014, vol. 50, # 68, p. 9690 - 9692
[5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 21, p. 3894 - 3897 |
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