Glycine → Benzyloxycarbonylglycine

HRID 1197221Notes

Reaction equation

HRID 1197221 reaction equation
[CH2:1]([O:8][C:9]([O:11]N1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][C:21]([OH:23])=[O:22].C(N(CC)CC)C>O>[CH2:1]([O:8][C:9]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 750GlycineHCID 8471TriethylamineHCID 83172Benzyl succinimido carbonate

Product 1

HCID 14349Benzyloxycarbonylglycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 50 ml of water was suspended 2.5 g of N-(benzyloxycarbonyloxy)succinimide, and the suspension was stirred for 1 hour at room temperature. To this suspension was added 20 ml of an aqueous solution of 0.75 g of glycine and 1.4 ml of triethylamine, and the reaction mixture was stirred for 12 hours as it was, but the desired product, benzyloxycarbonylglycine, could not be obtained.

Workup

  1. stirringthe reaction mixture was stirred for 12 hours as it

Sources & evidence

ORD record
ord-7dd79d3203d14144b06150e0ac1c26d0
Source dataset
uspto-grants-1992_05
Patent number
US05117031

Reaction notes

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