Acetyl chloride → HCID 140552480, compound

HRID 2092496Notes

Reaction equation

HRID 2092496 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][C:11](=[O:35])[NH:12][C:13]1[C:14]([CH3:34])=[N:15][O:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31](=[NH:33])[NH2:32])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)[CH3:9].C(N(C(C)C)CC)(C)C.[C:45](Cl)(=[O:47])[CH3:46]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][C:11](=[O:35])[NH:12][C:13]1[C:14]([CH3:34])=[N:15][O:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][C:31]([NH:32][C:45](=[O:47])[CH3:46])=[NH:33])=[CH:28][CH:29]=2)=[CH:20][CH:19]=1)[CH3:9]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 81531DiisopropylethylamineHCID 68204870HCID 68204870, compound

Product 1

HCID 140552480HCID 140552480, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [5-(4′-carbamimidoylmethyl-biphenyl-4-yl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl ester (0.055 g, 0.12 mmol) in dichloromethane (5 mL) was added diisopropylethylamine (0.052 mL, 0.3 mmol), followed by acetyl chloride (0.009 mL, 0.126 mmol), and the reaction was stirred at room temperature. Additional acetyl chloride (0.009 mL, 0.126 mmol) was added, and the reaction was stirred at room temperature. The mixture was quenched with water and extracted with dichloromethane. The combined organic layers were dried, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature
  2. customThe mixture was quenched with water
  3. extractionextracted with dichloromethane
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9b1bec9668d54c08bffb180d9a0eb217
Source dataset
uspto-grants-2013_05
Patent number
US08440707B2

Reaction notes

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