Diisopropylethylamine → HCID 76509286, compound

HRID 550950Notes

Reaction equation

HRID 550950 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C>ClCCl.CS(C)=O>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9][CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 24729723HCID 24729723, compound

Product 1

HCID 76509286HCID 76509286, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1-cyclohexyl-3-hydroxypropyl)carbamic acid tert-butyl ester (500 mg; 1.9 mmol) and N,N-diisopropylethylamine (1.35 mL; 7.8 mol) in dichloromethane (5 mL) was added a solution of pyridine sulfur trioxide complex (1.25 g; 7.8 mmol) in dimethyl sulfoxide (5 mL) at −20° C. The reaction mixture was stirred for 2 h and diluted with dichloromethane (20 mL). The reaction mixture was washed with 10% acetic acid in water (2×15 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude oil was used in the next step without further purification.

Workup

  1. washThe reaction mixture was washed with 10% acetic acid in water (2×15 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude oil was used in the next step without further purification

Sources & evidence

ORD record
ord-d02ea262337d431ba263de22ca689352
Source dataset
uspto-grants-2011_05
Patent number
US07947710B2

Reaction notes

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