Acetyl chloride → HCID 73295231, compound

HRID 1485887Notes

Reaction equation

HRID 1485887 reaction equation
C([Cl:4])(=O)C.C(O[C:10](=O)[N:11]([C@H:13]([C:15](=[O:46])[NH:16][C@@H:17]([CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)[C:18]([N:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:21]1[C:29](=[O:39])[NH:30][C:31]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=1[F:38])=[O:19])[CH3:14])C)(C)(C)C>CO>[ClH:4].[F:38][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]([F:37])[C:31]=1[NH:30][C:29]([C@@H:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:28][N:20]1[C:18](=[O:19])[C@H:17]([CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)[NH:16][C:15](=[O:46])[C@@H:13]([NH:11][CH3:10])[CH3:14])=[O:39]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 118252521HCID 118252521, compound

Product 1

HCID 73295231HCID 73295231, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of acetyl chloride (552 mg, 500 μL, 7.03 mmol, Eq: 24.2) in MeOH (2 mL) was added to a vial containing ((S)-1-{(S)-1-Cyclohexyl-2-[(S)-1-(2,6-di fluoro-phenylcarbamoyl)-1,3-dihydro-iso indol-2-yl]-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester (174 mg, 291 μmol, Eq: 1.00). The mixture was stirred at RT for 1 h. The solvent was evaporated and the resulting solid was redissolved in MeCN (3 mL) and water (1 mL). It was lyophilized to give (S)-2-[(S)-2-Cyclohexyl-2-((S)-2-methylamino-propionylamino)-acetyl]-2,3-dihydro-1H-isoindole-1-carboxylic acid (2,6-difluoro-phenyl)-amide hydrochloride (148 mg) as a white powder, m/z=499 (M+H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting solid was redissolved in MeCN (3 mL)

Sources & evidence

ORD record
ord-fdb5d8ed77d64b23bd356e50e8b9aa72
Source dataset
uspto-grants-2016_08
Patent number
US09422332B2

Reaction notes

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