Trifluoroacetic acid → Trifluoroacetic acid

HRID 1095087Notes

Reaction equation

HRID 1095087 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[CH:23]2[C:28]3([C:36]4[C:31](=[CH:32][C:33]([Cl:37])=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:38])[CH:27]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=3)[CH2:26][C:25](=[O:46])[NH:24]2)[CH2:11][CH2:10]1)=[O:7])(C)(C)C.[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50]>ClCCl>[Cl:37][C:33]1[CH:32]=[C:31]2[NH:30][C:29](=[O:38])[C:28]3([CH:27]([C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=4)[CH2:26][C:25](=[O:46])[NH:24][CH:23]3[C:17]3[CH:18]=[C:19]([I:22])[CH:20]=[CH:21][C:16]=3[O:15][CH:12]3[CH2:13][CH2:14][N:9]([CH2:8][C:6]([OH:7])=[O:5])[CH2:10][CH2:11]3)[C:36]2=[CH:35][CH:34]=1.[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 74931359HCID 74931359, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 86631792HCID 86631792, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of racemic(2′R, 3R, 4′S)-2′-[2-(1-tert-butoxycarbonylmethyl-4-piperidinyloxy)-5-iodo-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.22 g, 0.28 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL). The reaction mixture was stirred at room temperature for 18 h, then concentrated. The residue was triturated with dichlormethane and hexanes to give racemic(2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[2-(1-hydroxycarbonylmethyl-4-piperidinyloxy)-5-iodo-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as trifluoroacetic acid salt: yellow solid (Yield 0.18 g)

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with dichlormethane and hexanes

Sources & evidence

ORD record
ord-ce06e4c07c6449eb92f15bd52fc822a0
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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