Water → HCID 75487703, compound

HRID 1796850Notes

Reaction equation

HRID 1796850 reaction equation
[OH:1][CH2:2][C@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:5][S:6][CH3:7].C(N(CC)CC)C.O.OS([O-])(=O)=O.[K+]>CS(C)=O>[CH:2]([C@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:4][CH2:5][S:6][CH3:7])=[O:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 44593821tert-Butyl [(2R)-1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

Product 1

HCID 75487703HCID 75487703, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 1A (9.05 g, 38.5 mmol), sulfur trioxide pyridine complex (30.64 g, 192.5 mmol), and triethylamine (26.8 mL, 192.5 mmol) in DMSO (30 mL) was stirred at ambient temperature for 30 minutes, cooled to 0° C., treated sequentially with water (20 mL) and saturated aqueous KHSO4 (120 mL), and extracted with ethyl acetate. The extract was washed sequentially with saturated aqueous KHSO4 and brine, dried (MgSO4), filtered, and concentrated to provide the desired product (9.00 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed sequentially with saturated aqueous KHSO4 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2976f0f48d854573bc2dbe4a8a6fb534
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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