Acetyl chloride → HCID 68408593, compound

HRID 2264839Notes

Reaction equation

HRID 2264839 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][CH:18]=3)=[CH:11][CH:10]=2)[N:5]1C(OC(C)(C)C)=O)=[O:3].C([Cl:33])(=O)C>C(OCC)(=O)C.CO>[ClH:33].[C:17]1([CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9]([C@@H:6]3[NH:5][C@H:4]([C:2]([NH2:1])=[O:3])[CH2:8][CH2:7]3)=[CH:10][CH:11]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 6367Acetyl chloride2×HCID 59164836HCID 59164836, compound

Product 1

HCID 68408593HCID 68408593, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-[(phenylmethyl)oxy]phenyl)-1-pyrrolidinecarboxylate (D12, 45 mg, 0.113 mmol) in a mixture of ethyl acetate and methanol (9/1, 1 ml) was added acetyl chloride (20 μl, 0.282 mmol) at 0° C. The mixture was shaken for 1.5 h and slowly allowed to warm to room temperature. After 4 h under these conditions, additional acetyl chloride (20 μl, 0.654 mmol) was added. After evaporating the solvent, the residue was triturated with diethyl ether to afford the title compound as a white solid (25 mg, 66%); Rt (HPLC): 3.55 min; 1H NMR (300 MHz, DMSO-d6) δ (ppm): 10.50 (bs, 1H); 8.15 (bs, 1H); 8.05 (s, 1H); 7.73 (s, 1H); 7.42-7.49 (m, 4H); 7.40 (t, 2H); 7.30-7.36 (m, 1H); 7.08 (d, 2H); 5.15 (s, 2H); 4.60 (dd, 1H); 4.30 (dd, 1H); 2.23-2.40 (m, 2H); 2.10-2.20 (m, 1H); 1.95-2.08 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-b8e91cf313c846d68f91ae0c68730192
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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