Triethylamine → Methyl N-benzyloxycarbonylglycinate

HRID 1283770Notes

Reaction equation

HRID 1283770 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](N(CC)CC)C.COC(ON=C(C#N)C(N)=O)=O>C(Cl)(Cl)Cl.C(#N)C>[CH3:16][O:14][C:13](=[O:15])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 14349BenzyloxycarbonylglycineHCID 54246101HCID 54246101, compound

Product 1

HCID 71033Methyl N-benzyloxycarbonylglycinate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-benzyloxycarbonylglycine (1.05 g) and triethylamine (0.7 ml) in chloroform (10 ml) and acetonitrile (5 ml), 2-methoxycarbonyloxyimino-2-cyanoacetic acid amide (0.85 g) is added, and the resulting mixture is stirred at room temperature for 1 hour and allowed to stand over night. The reaction mixture is treated as in Example A to give N-benzyloxycarbonylglycine methyl ester (1.1 g) as an oil.

Workup

  1. waitto stand over night
  2. additionThe reaction mixture is treated as in Example A

Sources & evidence

ORD record
ord-a6ff67c2293049cdbe48b468b27a72ff
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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