Chloroacetyl chloride → HCID 89545092, compound

HRID 2283406Notes

Reaction equation

HRID 2283406 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]2[C:16]([F:33])=[C:17]([C@H:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:23][CH3:24])[CH:18]=[CH:19][C:20]=2[Cl:21])=[O:14])=[CH:9][C:8]=1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)CC)C>ClCCl>[CH2:35]([O:34][C:8]1[CH:9]=[C:10]([C:13]([C:15]2[C:16]([F:33])=[C:17]([C@H:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:23][CH3:24])[CH:18]=[CH:19][C:20]=2[Cl:21])=[O:14])[CH:11]=[CH:12][C:7]=1[NH:6][C:3](=[O:4])[CH2:2][Cl:1])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 8471TriethylamineHCID 117874973HCID 117874973, compound

Product 1

HCID 89545092HCID 89545092, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 4 Chloroacetyl chloride (0.323 ml, 4.05 mmol) was added to a mixture of tert-butyl N-[(1R)-1-(3-{[4-amino-3-(benzyloxy)phenyl]carbonyl}-4-chloro-2-fluorophenyl)propyl]carbamate (1.6 g, 3.12 mmol), triethylamine (0.651 ml, 4.68 mmol) and dichloromethane (30 ml) at room temperature. After 30 minutes a small additional portion of chloroacetyl chloride was added and in 60 minutes the reaction was complete. The reaction mixture was washed with dilute citric acid solution and dilute sodium bicarbonate and then concentrated. The residue was purified on silica eluting with 30-70% ethyl acetate/petrol to furnish tert-butyl N-[(1R)-1-(3-{[3-(benzyloxy)-4-(2-chloroacetamido)-phenyl]-carbonyl}-4-chloro-2-fluorophenyl)propyl]carbamate as a yellow oil (1.754 g). [M−H]−=587

Workup

  1. washThe reaction mixture was washed with dilute citric acid solution and dilute sodium bicarbonate
  2. concentrationconcentrated
  3. customThe residue was purified on silica eluting with 30-70% ethyl acetate/petrol

Sources & evidence

ORD record
ord-ab3c982c0fa94df3b13ba445c702f6a9
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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