Acetyl chloride → HCID 68411334, compound

HRID 2264842Notes

Reaction equation

HRID 2264842 reaction equation
[NH2:1][C:2]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])=[CH:11][C:10]=2[F:24])[N:5]1C(OC(C)(C)C)=O)=[O:3].C([Cl:35])(=O)C>C(OCC)(=O)C.CO>[ClH:35].[F:24][C:10]1[CH:11]=[C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH:13]=[CH:14][C:9]=1[C@@H:6]1[NH:5][C@H:4]([C:2]([NH2:1])=[O:3])[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 59596675HCID 59596675, compound

Product 1

HCID 68411334HCID 68411334, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(2-fluoro-4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-pyrrolidinecarboxylate (D47, 130 mg, 0.300 mmol) in a mixture of ethyl acetate (2.3 ml) and methanol (0.230 ml) was added acetyl chloride (64 μl, 2.5 eq) at 0° C. The mixture was shaken for 2 h and slowly allowed to warm to room temperature. After evaporating the solvent, the residue was triturated with diethyl ether to afford the title compound as a white solid (101 mg, 92%); Rt (HPLC): 3.66 min; MS: (ES/+) m/z: 333 [MH+], C18H18F2N2O2 requires 332; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.36 (br. s., 1H), 8.35 (br. s., 1H), 8.04 (s, 1H), 7.72 (s, 1H), 7.51-7.64 (m, 2H), 7.40-7.49 (m, 1H), 7.20-7.32 (m, 2H), 7.05 (dd, 1H), 6.98 (dd, 1H), 5.19 (s, 2H), 4.81 (dd, 1H), 4.31 (dd, 1H), 2.22-2.42 (m, 2H), 2.01-2.22 (m, 2H).

Workup

  1. customAfter evaporating the solvent
  2. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9e5e9dd312374188806425a04a237618
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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