Water → HCID 58017472, compound

HRID 1879232Notes

Reaction equation

HRID 1879232 reaction equation
[CH2:1]([N:4]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)(=[O:22])=[O:21])[C@@H:5]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7])[CH:2]=[CH2:3].B.CSC.B1([O-])O[O:36]1.O.O.O.O.[Na+].O>C1COCC1>[OH:36][CH2:3][CH2:2][CH2:1][N:4]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)(=[O:22])=[O:21])[C@@H:5]([C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 12423031(Dimethyl sulfide)trihydroboronHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 68999085HCID 68999085, compound

Product 1

HCID 58017472HCID 58017472, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl N-allyl-N-[(3-methoxyphenyl)sulfonyl]-3-methyl-D-valinate (12.7 g, 29.3 mmol) in THF (90 mL) cooled to 0° C., borane-DMS complex (5M in diethyl ether, 12 mL, 60.0 mmol) is added dropwise. The reaction mixture is slowly warmed up to rt and is allowed to stir at rt for 24 h. To the reaction mixture, sodium perborate tetrahydrate (27.1 g, 176 mmol) and de-ionized water (90 mL) are added in portions. The reaction mixture is stirred for additional 3 h. The reaction mixture is filtered to remove the white precipitates, then the aqueous layer is extracted with EtOAc. The organic extracts are combined, washed with brine, dried over sodium sulfate, and concentrated in vacuo to obtain a highly viscous yellow oil. The crude product is purified by column chromatography eluting with a gradient of 25-65% EtOAc/heptane to obtain the desired alcohol as a colorless oil (9.08 g). Mass spectrum (450.46; M+1).

Workup

  1. stirringThe reaction mixture is stirred for additional 3 h
  2. filtrationThe reaction mixture is filtered
  3. customto remove the white precipitates
  4. extractionthe aqueous layer is extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a highly viscous yellow oil
  9. customThe crude product is purified by column chromatography
  10. washeluting with a gradient of 25-65% EtOAc/heptane

Sources & evidence

ORD record
ord-72152754cf9242f5a6aad31b328dd8ec
Source dataset
uspto-grants-2012_11
Patent number
US08314148B2

Reaction notes

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