Water → HCID 68293071, compound

HRID 1424688Notes

Reaction equation

HRID 1424688 reaction equation
[CH3:1][C@@H:2]1[S:7][C:6]2[S:8][C:9]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:10][C:5]=2[C:4](=[O:15])[CH2:3]1.C(N(CC)CC)C.O>CCN(CC)CC.C(O)=O.C(O)=O.C(#N)C>[OH:15][CH:4]1[CH2:3][C@H:2]([CH3:1])[S:7][C:6]2[S:8][C:9]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:10][C:5]1=2

Participants

7

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 51897763HCID 51897763, compound

Product 1

HCID 68293071HCID 68293071, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 6342AcetonitrileSolventHCID 11084032Triethylammonium formateSolvent

Conditions

Temperature
28 °C

Procedure

A solution of catalyst RuCl(p-cymene)[(S,S)-Fs-DPEN] (27.4 mg, 0.0385 mmol) in TEAF (1.5 g, molar ratio 5:2) was added to a mixture of (6S)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide (1.0 g, 3.80 mmol) in formic acid:triethylamine (2.16 g, molar ratio 5:2) under nitrogen at 28° C. After 16 hours, a solution composed of RuCl(p-cymene)[(S,S)-Fs-DPEN] (27.5 mg, 0.0386 mmol) in acetonitrile (1.2 g) was added to the mixture. After five days of stirring at 28° C., demineralised water (10.7 g) was added to the reagent mixture and the temperature was lowered to 10° C. The solid was filtered to obtain (6S)-4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide as a mixture of trans:cis diastereoisomers equal to 61.7:38.3 (0.32 g, yield 32%).

Workup

  1. customat 28° C
  2. additionwas added to the mixture
  3. customwas lowered to 10° C
  4. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-ae5ddc52e1e44cafa9952b652054a554
Source dataset
uspto-grants-2015_01
Patent number
US08927740B2

Reaction notes

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