Acetyl chloride → HCID 66700844, compound

HRID 1690130Notes

Reaction equation

HRID 1690130 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@@:18]3([CH2:24][CH2:23][NH:22][C:21]3=[O:25])[N:17]2C(OC(C)(C)C)=O)=[CH:12][CH:11]=1.C([Cl:36])(C)=O>C(OCC)(=O)C.CO>[ClH:36].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:16]2[CH2:20][CH2:19][C@@:18]3([CH2:24][CH2:23][NH:22][C:21]3=[O:25])[NH:17]2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 59468939HCID 59468939, compound

Product 1

HCID 66700844HCID 66700844, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S,5S)-2-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (D79, 130 mg, 0.295 mmol) in a mixture of ethyl acetate (2.7 ml) and methanol (0.3 ml) at 0° C. was added AcCl (130 μl, 1.82 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 (80 mg, 82%); Rt (HPLC) 3.60 min; MS: (ES/+) m/z: 341 [MH+] C20H21FN2O2 requires 340; 1H NMR (500 MHz, DMSO-d6) δ(ppm): 10.37 (br. s, 1H), 8.78 (br. s, 1H), 8.42 (s, 1H), 7.53-7.58 (m, 1H), 7.54 (d, 2H), 7.42 (dd, 1H), 7.25 (t, 1H), 7.23 (t, 1H), 7.10 (d, 2H), 5.13-5.21 (m, 2H), 4.65-4.76 (m, 1H), 3.25-3.33 (m, 2H), 2.48-2.55 (m, 1H), 2.31-2.42 (m, 2H), 2.27-2.34 (m, 2H), 2.04-2.14 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-43d42f347a6043eaa54f4f43ad824525
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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