Glycine → Boc-(D)-Chg-Gly-OH

HRID 2298747Notes

Reaction equation

HRID 2298747 reaction equation
[NH:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@@H:2]([C:9]([OH:11])=O)[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:34][CH2:35][C:36]([OH:38])=[O:37].C([O-])(O)=O.[Na+]>COCCOC.O>[NH:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@@H:2]([C:9]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:11])[CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 750GlycineHCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 7014890(2R)-[(tert-Butoxycarbonyl)amino](cyclohexyl)acetic acid

Product 1

HCID 131723715Boc-(D)-Chg-Gly-OHYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

8.1 g (31.5 mmol) of Boc-(D)-Chg-OH were dissolved in 100 ml of 1,2-dimethoxyethane and then, at 0° C., NHS (3.7 g, 32.0 mmol) and DCC (7.0 g, 34.0 mmol) were added. After 6 h at RT, DCH was filtered off, and a solution of 2.3 g (31.0 mml) of glycine and 2.6 g (31.0 mmol) of NaHCO3 in 350 ml of water was added to the filtrate. Stirring at RT for 24 h was followed by concentration and extraction with 5% citric acid/ethyl acetate. Concentration of the organic phase resulted in 8.2 g (85.0%) of product.

Workup

  1. filtrationDCH was filtered off
  2. concentrationwas followed by concentration and extraction with 5% citric acid/ethyl acetate

Sources & evidence

ORD record
ord-8123e690eec74f21b47b6d8239844d3b
Source dataset
uspto-grants-2002_12
Patent number
US06495336B1

Reaction notes

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