Methylamine ethanol → HCID 67750310, compound

HRID 1755754Notes

Reaction equation

[CH3:1][NH2:2].C(O)C.[CH2:6]([O:8][C:9](=[O:38])[CH:10]=[CH:11][C@@H:12]1[CH2:16][C@@H:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][N:13]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1)=[O:26])[CH3:7]>>[CH2:6]([O:8][C:9](=[O:38])[CH2:10][CH:11]([NH:2][CH3:1])[C@@H:12]1[CH2:16][C@@H:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][N:13]1[C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=1)=[O:26])[CH3:7]

Participants

Reactant 2

HCID 22028356Methylamine ethanol

HCID 57028905HCID 57028905, compound

Product 1

HCID 67750310HCID 67750310, compoundYield 53.3%

Procedure

A 5.3M methylamine-ethanol solution (5 ml, 26.6 mmol) was added to 3-[(2S,4R)-4-tert-butyldimethylsiloxy-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]acrylic acid ethyl ester (2.94 g, 6.15 mmol, compound of Reference Example 1-6 of Japanese Patent Application No. 342,948/1989) at room temperature, and the mixture was left to stand at the same temperature for 2 days. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (Wakogel™ C-300, ethyl acetate) to obtain 3-methylamino-3-[(2S,4R)-4-tert-butyldimethylsiloxy-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]propionic acid ethyl ester (1.67 g, yield: 53.3%).

Workup

wait342,948/1989) at room temperature, and the mixture was left
concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-1a889a2fb96d4024b9108534781307a7
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438054

Reaction notes

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