Glycine → Benzyloxycarbonylglycine

HRID 1722882Notes

Reaction equation

HRID 1722882 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-f748f6ca1c40421c84ca38e19c3063c1
Source dataset
uspto-grants-1989_08
Patent number
US04857656

Reaction notes

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