Acetyl chloride → HCID 73295401, compound

HRID 1485893Notes

Reaction equation

HRID 1485893 reaction equation
C([Cl:4])(=O)C.C(O[C:10](=O)[N:11]([C@H:13]([C:15](=[O:47])[NH:16][C@@H:17]([CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[C:18]([N:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:21]1[C:30](=[O:40])[NH:31][C:32]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=1[F:39])=[O:19])[CH3:14])C)(C)(C)C>CO>[ClH:4].[F:39][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]([F:38])[C:32]=1[NH:31][C:30]([C@@H:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:28][CH2:29][N:20]1[C:18](=[O:19])[C@H:17]([CH:41]1[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]1)[NH:16][C:15](=[O:47])[C@@H:13]([NH:11][CH3:10])[CH3:14])=[O:40]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 90040598HCID 90040598, compound

Product 1

HCID 73295401HCID 73295401, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of acetyl chloride (552 mg, 500 μL, 7.03 mmol, Eq: 74.3) in MeOH (2 mL) was added to a vial containing ((S)-1-{(S)-1-cyclohexyl-2-[(S)-1-(2,6-di fluoro-phenylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester (58 mg, 94.7 μmol, Eq: 1.00). The mixture was stirred at RT for 1 h. The solvent was evaporated and the resulting solid was dissolved in MeCN (3 mL) and water (1 mL) and the solution lyophilized to give (S)-2-[(S)-2-cyclohexyl-2-((S)-2-methylamino-propionylamino)-acetyl]-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid (2,6-difluoro-phenyl)-amide hydrochloride (50 mg) as a white powder (50 mg), m/z=513 (M+H).

Workup

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

Sources & evidence

ORD record
ord-4e704c28fb894ffbbed249a2ed975f15
Source dataset
uspto-grants-2016_08
Patent number
US09422332B2

Reaction notes

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