Acetyl chloride → HCID 73294890, compound

HRID 1485899Notes

Reaction equation

HRID 1485899 reaction equation
C([Cl:4])(=O)C.C(O[C:10](=O)[N:11]([C@H:13]([C:15](=[O:44])[NH:16][C@H:17]([C:21]([N:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@H:24]1[C:33](=[O:43])[NH:34][C:35]1[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=1[Cl:42])=[O:22])[CH:18]([CH3:20])[CH3:19])[CH3:14])C)(C)(C)C>CO>[ClH:4].[Cl:42][C:36]1[CH:37]=[CH:38][CH:39]=[C:40]([F:41])[C:35]=1[NH:34][C:33]([C@@H:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:31][CH2:32][N:23]1[C:21](=[O:22])[C@@H:17]([NH:16][C:15](=[O:44])[C@@H:13]([NH:11][CH3:10])[CH3:14])[CH:18]([CH3:19])[CH3:20])=[O:43]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 90040531HCID 90040531, compound

Product 1

HCID 73294890HCID 73294890, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of acetyl chloride (552 mg, 500 μL, 7.03 mmol, Eq: 115) in MeOH (2 mL) was added to a vial containing ((S)-1-{(S)-1-[(S)-1-(2-chloro-6-fluoro-phenylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]-2-methyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester (36 mg, 61.1 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) which was lyophilized to give (S)-2-[(S)-3-methyl-2-((S)-2-methylamino-propionylamino)-butyryl]-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid (2-chloro-6-fluoro-phenyl)-amide hydrochloride (30 mg) as a white powder, m/z=489 (M+H).

Workup

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

Sources & evidence

ORD record
ord-8389ba6430e143cfbb7b8d097aa972a3
Source dataset
uspto-grants-2016_08
Patent number
US09422332B2

Reaction notes

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