Acetyl chloride → HCID 66700195, compound

HRID 1690128Notes

Reaction equation

HRID 1690128 reaction equation
[NH2:1][C:2]([C@:4]1([CH2:33][O:34][CH3:35])[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])=[C:11]([O:24][CH3:25])[CH:10]=2)[N:5]1C(OC(C)(C)C)=O)=[O:3].C([Cl:39])(C)=O>C(OCC)(=O)C.CO>[ClH:39].[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C@@H:6]2[NH:5][C@:4]([CH2:33][O:34][CH3:35])([C:2]([NH2:1])=[O:3])[CH2:8][CH2:7]2)=[CH:10][C:11]=1[O:24][CH3:25]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 59468958HCID 59468958, compound

Product 1

HCID 66700195HCID 66700195, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl (2R,5R)-2-(aminocarbonyl)-5-[4-{[(2-fluorophenyl)methyl]oxy}-3-(methyloxy)phenyl]-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate (D65, 70 mg, 0.14 mmol) in a mixture of ethyl acetate (1.8 ml) and methanol (0.2 ml) at 0° C. was added AcCl (170 μl, 2.38 mmol). The mixture was stirred for 4 hours at room temperature. The solvent was evaporated and the residue was triturated with Et2O to afford the title compound as a white solid (49 mg, 82%); Rt (HPLC) 3.62 min; MS: (ES/+) m/z: 389 [MH]+ C21H25FN2O4 requires 388; 1H NMR (500 MHz, DMSO-d6) δ (ppm): 9.91-10.02 (br.s, 1H); 8.07-8.25 (br.s, 2H); 7.94-8.03 (br.s, 1H); 7.50 (t, 1H); 7.35-7.43 (m, 1H); 7.17-7.25 (m, 2H); 7.13 (s, 1H); 7.06 (d, 1H); 6.95 (dd, 1H); 5.08 (s, 2H); 4.51-4.66 (m, 1H); 3.92 (d, 1H); 3.74 (s, 3H); 3.69 (d, 1H); 3.26 (s, 3H); 2.17-2.35 (m, 2H); 1.97-2.12 (m, 1H); 1.79-1.96 (m, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-dcadd922d9d7407a8d7a6efec20b0c5a
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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