Methyl chloroformate → HCID 56973781, compound

HRID 1833831Notes

Reaction equation

HRID 1833831 reaction equation
[CH3:1][O:2][C:3](Cl)=[O:4].C(N(CC)CC)C.[C:13]([NH:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=1)([CH3:16])([CH3:15])[CH3:14]>CC(C)=O>[C:13]([NH:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:3]([O:2][CH3:1])=[O:4])[CH:21]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 28689665HCID 28689665, compound

Product 1

HCID 56973781HCID 56973781, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
17.5 °C

Procedure

10.45 g (0.1 mol) of chloroformic acid methyl ester, followed by 10.1 g (0.1 mol) of triethylamine, were added dropwise to a solution of 20.6 g (0.1 mol) of 3-amino-phenylacetic acid tert.-butylamide in 200 ml of acetone whilst cooling at 15 to 20° C. The mixture was stirred for a further 2 hours at room temperature, the triethylamine hydrochloride which had precipitated was filtered off and the filtrate was concentrated by evaporation under reduced pressure. The residue which hereupon remained was stirred with very dilute hydrochloric acid, filtered off, dried and recrystallized from a little carbon tetrachloride. 22 g (83.5% of theory) of 3-methoxycarbonylamino-phenylacetic acid tert.-butylamide of melting point 123°-124° C were obtained.

Workup

  1. customthe triethylamine hydrochloride which had precipitated
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. stirringThe residue which hereupon remained was stirred with very dilute hydrochloric acid
  5. filtrationfiltered off
  6. customdried
  7. customrecrystallized from a little carbon tetrachloride

Sources & evidence

ORD record
ord-43487cc559164cc490c9b6dcefb93e70
Source dataset
uspto-grants-1978_01
Patent number
US04067726

Reaction notes

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