Ethyl chloroformate → HCID 68001050, compound

HRID 535339Notes

Reaction equation

HRID 535339 reaction equation
C(N(C(C)C)CC)(C)C.Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12].[NH2:16][CH:17]([CH2:31][C:32]1([F:37])[CH2:36][CH2:35][CH2:34][CH2:33]1)[C:18]([NH:20][C:21]1([CH:26]([C:28](=[O:30])[NH2:29])[OH:27])[CH2:24][CH:23]([F:25])[CH2:22]1)=[O:19].C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl>[CH2:14]([O:13][C:11](=[O:12])[NH:16][CH:17]([C:18](=[O:19])[NH:20][C:21]1([CH:26]([C:28](=[O:30])[NH2:29])[OH:27])[CH2:22][CH:23]([F:25])[CH2:24]1)[CH2:31][C:32]1([F:37])[CH2:36][CH2:35][CH2:34][CH2:33]1)[CH3:15]

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 68000554HCID 68000554, compound

Product 1

HCID 68001050HCID 68001050, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (0.087 mL, 0.5 mmol) and ethyl chloroformate (0.024 mL, 0.25 mmol) were added to a stirred solution of the amine A1-b, 2-amino-N-[1-(carbamoyl-hydroxy-methyl)-3-fluoro-cyclobutyl]-3-(1-fluorocyclopentyl)-propionamide (0.23 mmol) in DMF. After 15 min sat. aq. NaHCO3 and DCM were added and the organic layer was collected and concentrated and purified on flash silica gel column using DCM-MeOH 0-10% which gave the title compound (62 mg) [M+1]+391.9.

Workup

  1. customthe organic layer was collected
  2. concentrationconcentrated
  3. custompurified on flash silica gel column

Sources & evidence

ORD record
ord-60095ca2eab44443806a488a0a64721c
Source dataset
uspto-grants-2014_10
Patent number
US08859505B2

Reaction notes

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