Ethyl chloroformate → 2-(t-Butoxycarbonylaminoacetamido)-6-methylbenzyl alcohol

HRID 1762197Notes

Reaction equation

HRID 1762197 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC)=O.[NH2:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH2:22][OH:23].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH2:22][OH:23])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 15339417(2-Amino-6-methylphenyl)methanol

Product 1

HCID 143684552-(t-Butoxycarbonylaminoacetamido)-6-methylbenzyl alcoholYield 17.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of t-butoxycarbonylaminoacetic acid (3.5 g) in methylene chloride (50 ml) was added triethylamine (2.0 g) and then ethyl chloroformate (1.9 ml) with ice-cooling. After being stirred for 1 hour, 2-amino-6-methylbenzyl alcohol (2.74 g) was added thereto and the mixture was stirred for 7 days at an ambient temperature. To the mixture was added a saturated aqueous solution of sodium hydrogen carbonate and the organic layer was separated, washed with water and dried over magnesium sulfate. The solvent was distilled off and the residue was triturated with diethyl ether to give 2-(t-butoxycarbonylaminoacetamido)-6-methylbenzyl alcohol (1.04 g).

Workup

  1. stirringthe mixture was stirred for 7 days at an ambient temperature
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-4fd790f3f8f046329c6a27b83f363321
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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