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

HRID 1078118
Notes
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Reaction equation

HRID 1078118 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-47eba4c7f4354b9091aaac0071ab990f
Source dataset
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05545750

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes