Diisopropylethylamine → HCID 76509286, compound

HRID 2387397Notes

Reaction equation

HRID 2387397 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) The organic layer
  2. dry with materialwas 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-1d346679659f4ee6bff095f04ae1ec77
Source dataset
uspto-grants-2012_09
Patent number
US08268863B2

Reaction notes

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