Dimethyl Sulfoxide → HCID 86615385, compound

HRID 1436741Notes

Reaction equation

HRID 1436741 reaction equation
CS(C)=O.[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([O:18][CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:15][CH2:14][C@@H:13]1[CH2:28][OH:29])=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>>[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([O:18][CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:15][CH2:14][C@@H:13]1[CH:28]=[O:29])=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 86615386HCID 86615386, compound

Product 1

HCID 86615385HCID 86615385, compound

Procedure

Add sulfur trioxide pyridine complex (7.6 g, 47.8 mmol) in dimethylsulfoxide (27.0 mL, 382.4 mmol) to (2R, 5R)-5-Benzyloxymethoxy-2-hydroxymethyl-piperidine-1-carboxylic acid 1-tert-butyl ester (8.4 g, 23.90 mmol) in triethylamine (20.0 mL, 143.4 mmol) at 10° C. and stir at room temperature for 30 minutes. Add water and extract with diethyl ether. Combine the organic layers, wash with 5% citric acid followed by saturated aqueous sodium chloride. Dry over magnesium sulfate and concentrate to provide the desired compound. (8.0 g crude)

Workup

  1. extractionAdd water and extract with diethyl ether
  2. washwash with 5% citric acid
  3. dry with materialDry over magnesium sulfate
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-119e9e077841485eaa890905f3961aad
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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