Acetyl chloride → HCID 68410011, compound

HRID 2264846Notes

Reaction equation

HRID 2264846 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:20][CH2:19][C@@H:18]([C:21]([NH:23][CH3:24])=[O:22])[N:17]2C(OC(C)(C)C)=O)=[CH:12][CH:11]=1.C([Cl:35])(C)=O>C(OCC)(=O)C.CO>[ClH:35].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[NH:17][C@H:18]([C:21]([NH:23][CH3:24])=[O:22])[CH2:19][CH2:20]2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 59596672HCID 59596672, compound

Product 1

HCID 68410011HCID 68410011, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl (2R,5S)-2-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-5-[(methylamino)carbonyl]-1-pyrrolidinecarboxylate (D96, 40 mg, 0.09 mmol) in ethyl acetate (0.9 ml) and methanol (0.1 ml) at 0° C. was added AcCl (40 μl, 0.56 mmol) and the mixture was stirred for two hours at room temperature. The solvent was removed under nitrogen flow and the residue triturated with Et2O. The solvent was removed to afford the title compound as a white solid (28 mg, 85%). Rt (HPLC): 3.74 min; MS: (ES/+) m/z: 329-[MH+] C19H21FN2O2 requires 328; 1H NMR (500 MHz, DMSO-d6) δ (ppm): 10.03-10.78 (br.s, 1H); 8.56 (q, 1H); 7.95-8.46 (br.s, 1H); 7.55 (dt, 1H); 7.49 (d, 2H); 7.39-7.46 (m, 1H); 7.20-7.29 (m, 2H); 7.09 (d, 2H); 5.16 (s, 2H); 4.58 (dd, 1H); 4.28 (dd, 1H); 2.70 (d, 3H); 2.21-2.37 (m, 2H); 1.98-2.17 (m, 2H).

Workup

  1. customThe solvent was removed under nitrogen flow
  2. customthe residue triturated with Et2O
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-3e283bba3bf94ae8994903c8b377b73e
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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