4-Methylmorpholine → 2,4-Bis-((methyl)sulfonyl)amino-1,5-diphenyl-3-hydroxypentane

HRID 847585Notes

Reaction equation

HRID 847585 reaction equation
[NH2:1][CH:2]([CH:10]([OH:20])[CH:11]([NH2:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN1CCOCC1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[CH3:28][S:29]([NH:1][CH:2]([CH:10]([OH:20])[CH:11]([NH:19][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 46273942,4-Diamino-1,5-diphenylpentan-3-ol

Product 1

HCID 570690682,4-Bis-((methyl)sulfonyl)amino-1,5-diphenyl-3-hydroxypentaneYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the resultant compound of Example 12 (0.049 mmol) and 0.032 ml (0.29 mmol) of 4-methylmorpholine in 1 ml of dichloromethane was cooled to 0° C. and treated with 0.008 ml (0.10 mmol) of methanesulfonyl chloride. After 0.5 h, the solution was washed with 10% aqueous citric acid, dried over Na2SO4, and concentrated. Flash chromatography using 5% methanol in chloroform gave 2.6 mg (13%) of the desired compound. 1H NMR (CDCl3) δ 2.16 (s, 3H), 2.34 (s, 3H), 2.93 (m, 4H), 3.41 (d, J=4 Hz, 1H), 3.7-3.8 (m, 2H), 3.92 (m, 1H), 5.06 (d, J=9 Hz, 1H), 5.42 (d, J=9 Hz, 1 H), 7 2-7.4 (m, 10H). Mass spectrum (M+NH4)+ =444.

Workup

  1. washthe solution was washed with 10% aqueous citric acid
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-dd91b7ba9549473887604a0b931f4c81
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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