Triethylamine → methyl N-(p-nitrobenzyloxycarbonyl)-alpha-methoxyglycinate

HRID 2083802Notes

Reaction equation

HRID 2083802 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10].[CH3:22][O:23][CH:24]([C:26]([O:28][CH3:29])=[O:27])[NH2:25]>C(Cl)Cl>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:11][C:9]([NH:25][CH:24]([O:23][CH3:22])[C:26]([O:28][CH3:29])=[O:27])=[O:10])=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 782054-Nitrobenzyl chloroformateHCID 22492298HCID 22492298, compound

Product 1

HCID 20357887methyl N-(p-nitrobenzyloxycarbonyl)-alpha-methoxyglycinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (5.06 g, 0.05 mole) and p-nitrobenzyl chloroformate (10.78 g, 0.05 mole) are added to an ice-cold solution of methyl α-methoxyglycinate (6.10 g, 0.05 mole) in dry CH2Cl2 (100 ml). The resulting mixture is stirred in the cold and under N2 for 2 hours, and then washed with 3 portions of water. The CH2Cl2 phase is dried over MgSO4, filtered, and evaporated in vacuo. Recrystallization of the residue affords pure methyl N-(p-nitrobenzyloxycarbonyl)-α-methoxyglycinate.

Workup

  1. washwashed with 3 portions of water
  2. dry with materialThe CH2Cl2 phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customRecrystallization of the residue

Sources & evidence

ORD record
ord-81eceef9546e4329b032433a5a1d21b3
Source dataset
uspto-grants-1978_04
Patent number
US04086423

Reaction notes

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