Dimethyl Sulfoxide → HCID 13755869, compound

HRID 980329Notes

Reaction equation

HRID 980329 reaction equation
CS(C)=O.[OH:5][CH2:6][CH:7]([S:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C@@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(C(C)C)CC)(C)C.ClCCl>C(OCC)(=O)C>[CH:6]([CH:7]([S:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C@@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:5]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 13755863HCID 13755863, compound

Product 1

HCID 13755869HCID 13755869, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of pyridinium-1-sulfonate (789 mg, 3 eq) and anhydrous dimethylsulfoxide (3.0 ml) was stirred at room temperature under argon. After 15 minutes, a solution of (1S)-[3-hydroxy-2-[[(4-methoxyphenyl)methyl]thio]-1(phenylmethyl)propyl]carbamic acid, 1,1-dimethylethyl ester (690 mg, 1.65 mmol), diisopropylethylamine (1.73 ml, 6 eq) and dry dichloromethane (5.0 ml) was added in one portion. After 15 minutes longer, the reaction was diluted with ethyl acetate and washed with water, 1N hydrochloric acid, 1N sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Concentration of the filtrate yielded (1S)-[1-[formyl[[(4-methoxyphenyl)methyl]thio]methyl]-2-phenylethyl]carbamic acid, 1,1-dimethylethyl ester as a yellow solid: 610 mg (1.47 mmol); Rf =0.59 (silica gel, benzene:ethyl acetate 4:1).

Workup

  1. waitAfter 15 minutes longer
  2. washwashed with water, 1N hydrochloric acid, 1N sodium bicarbonate, brine
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-3dd3e11fa846457ca45b4ec00e09c137
Source dataset
uspto-grants-1987_01
Patent number
US04636560

Reaction notes

Loading…