Water → HCID 58869132, compound

HRID 2355200Notes

Reaction equation

HRID 2355200 reaction equation
[C:1]([O:5][C:6](=[O:28])[N:7]([CH3:27])[CH2:8][CH:9]1[CH2:18][C:17](=[O:19])[C:16]2[C:11](=[CH:12][C:13]([S:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:14][CH:15]=2)[O:10]1)([CH3:4])([CH3:3])[CH3:2].C(#N)C.CO.[OH2:34].OOS([O-])=O.[K+].[OH2:41]>>[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:8][CH:9]1[CH2:18][C:17](=[O:19])[C:16]2[C:11](=[CH:12][C:13]([S:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:41])=[O:34])=[CH:14][CH:15]=2)[O:10]1)[CH3:27])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 21864137Acetonitrile methanol waterHCID 23707502Potassium hydroxy sulfiteHCID 58869197HCID 58869197, compound

Product 1

HCID 58869132HCID 58869132, compoundYield 86%

Procedure

To a solution of methyl-(4-oxo-7-phenylsulfanyl-chroman-2-ylmethyl)-carbamic acid tert-butyl ester (200 mg, 0.5 mmol) in a mixture acetonitrile/methanol/water (1/1/1, 30 mL) was added oxone (922 mg, 1.5 mmol), and the reaction was stirred at room temperature for 1 hour. The mixture was then diluted with water and the solid was filtered off. The filtrate was concentrated in vacuo to give (7-benzenesulfonyl-4-oxo-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (186 mg, 86% yield) as yellow glass which was used without further purification for deprotection in the next step.

Workup

  1. filtrationthe solid was filtered off
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-38b22d61626743fba20a6eb7fb452272
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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