Diazomethane → (S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate

HRID 1261862Notes

Reaction equation

HRID 1261862 reaction equation
[C:1]([O:5][C:6](=[O:21])[C@H:7]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:24])=[N-]>CO>[C:1]([O:5][C:6](=[O:21])[C@H:7]([CH2:16][CH2:17][C:18]([O:20][CH3:24])=[O:19])[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid

Product 1

HCID 11120686(S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.3 g of N-tert.butyloxycarbonyl-L-glutamic acid 1-tert.-butyl ester (7.58 mmol) are dissolved in 80 ml of methanol and a freshly prepared diazomethane solution (23 mmol of Diazald®) is added dropwise at room temperature. After one hour, the solvent is removed under vacuum. The compound is purified using chromatography on silica gel. (column: 18.5*4 cm, DCM/MeOH=99/1, Rf=0.99).

Workup

  1. customthe solvent is removed under vacuum
  2. customThe compound is purified

Sources & evidence

ORD record
ord-1106764a6e1e4ec78c0282970da5c134
Source dataset
uspto-grants-2013_06
Patent number
US08471063B2

Reaction notes

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