Diazomethane → N-Boc-L-serine methyl ester

HRID 2399987Notes

Reaction equation

HRID 2399987 reaction equation
[C:1]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+](=[CH2:17])=[N-]>CCOCC>[CH3:17][O:13][C:12](=[O:14])[C@H:9]([CH2:10][OH:11])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 7019177N-Boc-L-serine methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of the acid (23) in ether (200 ml) at room temperature was treated with ethereal diazomethane until the yellow colour just persisted and tlc showed there to be no starting material present. The volatiles were then removed in vacuo leaving the product (24) as a light orange oil (17.89 g, 90%).

Workup

  1. customThe volatiles were then removed in vacuo

Sources & evidence

ORD record
ord-3389b9e0c13341b994f843b5358dc123
Source dataset
uspto-grants-1995_09
Patent number
US05451691

Reaction notes

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