Phosphorus sulfide (P2S5) → HCID 75293406, compound

HRID 658933Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][C:34]([CH3:45])([CH3:44])[C:35]([NH:37][S:38]([CH:41]2[CH2:43][CH2:42]2)(=[O:40])=[O:39])=[O:36])=[C:6]([CH:8]2[CH2:13][C:12](=O)[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:47]>C1COCC1.C1(C)C=CC=CC=1>[Cl:31][C:27]1[CH:26]=[C:25]2[NH:24][C:23](=[O:32])[C:9]3([CH:8]([C:6]4[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=4[O:33][C:34]([CH3:45])([CH3:44])[C:35]([NH:37][S:38]([CH:41]4[CH2:42][CH2:43]4)(=[O:39])=[O:40])=[O:36])[CH2:13][C:12](=[S:47])[NH:11][CH:10]3[C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:30]2=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of chiral (2′S, 3S, 4′R)-4′-[5-chloro-2-(2-cyclopropanesulfonylamino-1,1-dimethyl-2-oxo-ethoxy)-phenyl]-6-chloro-2′-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (12 mg, 0.018 mmol) and P2S5 (12 mg, 0.054 mmol) in THF (1 mL) was heated at 50° C. for 2 h, and then diluted with toluene (10 mL). The mixture was concentrated in vacuo and the residue was washed with DCM twice. The DCM layers were combined and concentrated. The residue was purified by flash chromatography to give the title compound as white solid (11 mg).

Workup

concentrationThe mixture was concentrated in vacuo
washthe residue was washed with DCM twice
concentrationconcentrated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-47d2c8d7059f4f8c90dfbe8d8306913f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076482B2

Reaction notes

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