Acetic Anhydride → 1-acetyl-6-chloro-4'-[5-chloro-2-(1-ethyl-1-methanesufonylaminocarbonyl-propoxy)-phenyl]-2'-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 658924Notes

Reaction equation

HRID 658924 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:45])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([CH2:34][CH3:35])([C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:28])[CH2:25][CH3:26])[CH2:14][C:13](=[O:36])[NH:12][CH:11]3[C:37]3[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=3[CH3:44])[C:5]2=[CH:4][CH:3]=1.[C:46](OC(=O)C)(=[O:48])[CH3:47]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:46]([N:8]1[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=2)[C:10]2([CH:15]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=3[O:23][C:24]([CH2:34][CH3:35])([C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:28])[CH2:25][CH3:26])[CH2:14][C:13](=[O:36])[NH:12][CH:11]2[C:37]2[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=2[CH3:44])[C:9]1=[O:45])(=[O:48])[CH3:47]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 749286676-chloro-4'-[5-chloro-2-(1-ethyl-1-methanesulfonylaminocarbonyl-propoxy)-phenyl]-2'-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 667698831-acetyl-6-chloro-4'-[5-chloro-2-(1-ethyl-1-methanesufonylaminocarbonyl-propoxy)-phenyl]-2'-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 23.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

At room temperature, to a mixture of racemic (2′S, 3S, 4′R)-6-chloro-4′-[5-chloro-2-(1-ethyl-1-methanesulfonylaminocarbonyl-propoxy)-phenyl]-2′-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (400 mg, 0.58 mmol) and acetic anhydride (71 mg, 0.69 mmol) in DCM (20 mL) was added DMAP (7 mg, 0.06 mmol) slowly. After the mixture was stirred for 2 h, the solution was washed by 0.5N HCl solution twice, dried over anhydrous Na2SO4 and concentrated. The residue was purified by Prep-HPLC to give the title compound as a white solid (100 mg).

Workup

  1. washthe solution was washed by 0.5N HCl solution twice
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-f1be3584a2d146a3b4c2d04cf68f55a0
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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