4-Toluenesulfonyl chloride → 2(t-Butyloxycarbonylamino)-4-(p-toluenesulfonylamino)-1,5-diphenyl-3-hydroxypentane

HRID 1379371Notes

Reaction equation

HRID 1379371 reaction equation
[NH2:1][CH:2]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:3]([OH:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>N1C=CC=CC=1.CCOCC>[C:16]([O:15][C:13]([NH:12][CH:4]([CH:3]([OH:20])[CH:2]([NH:1][S:34]([C:31]1[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=1)(=[O:36])=[O:35])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 147043774-Amino-2-(t-butyloxycarbonylamino)-1,5-diphenyl-3-hydroxypentane

Product 1

HCID 229101562(t-Butyloxycarbonylamino)-4-(p-toluenesulfonylamino)-1,5-diphenyl-3-hydroxypentane

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

The resultant compound of Example 11 (0.05 mmol) in 2 ml of pyridine was cooled to 0° C. and treated with 0.05 mmol of p-toluenesulfonyl chloride. After 2 h, the solution was diluted with ether, washed sequentially with 1N HCl, aqueous NaHCO3, and saturated brine, dried over MgSO4, and concentrated. Silica gel chromatography gave the desired compound.

Workup

  1. washwashed sequentially with 1N HCl, aqueous NaHCO3, and saturated brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e5b502b254cf414c9964feb8e11c2f0b
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

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