Acetyl chloride → HCID 68411591, compound

HRID 2264843Notes

Reaction equation

HRID 2264843 reaction equation
[NH2:1][C:2]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[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:11]2[CH:10]=[C:9]([C@@H:6]3[NH:5][C@H:4]([C:2]([NH2:1])=[O:3])[CH2:8][CH2:7]3)[CH:14]=[CH:13][CH:12]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 59596716HCID 59596716, compound

Product 1

HCID 68411591HCID 68411591, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-{3-[(phenylmethyl)oxy]phenyl}-1-pyrrolidinecarboxylate (D54, 142 mg, 0.358 mmol) in a mixture of ethyl acetate (2.3 ml) and methanol (0.23 ml) was added acetyl chloride (64 μl, 2.5 eq) at 0° C. The mixture was shaken for 1.5 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 (71 mg, 60%); Rt (HPLC): 3.51 min. MS: (ES/+) m/z: 297 [MH+], C18H20N2O2 requires 296; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.52 (br. s., 1H), 8.41 (br. s., 1H), 8.03 (s, 1H), 7.73 (s, 1H), 7.31-7.50 (m, 6H), 7.26 (t, 1H), 7.10 (d, 1H), 7.06 (dd, 1H), 5.13 (s, 2H), 4.62 (dd, 1H), 4.32 (dd, 1H), 2.24-2.44 (m, 2H), 2.09-2.23 (m, 1H), 1.93-2.09 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-f711ee55c8e342a7bafe873d1f1cded7
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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