Diisopropylethylamine → 1-Hydroxy-4-(4-(oxazol-4-yl)phenylsulfonamido)-N-(1-phenylethyl)cyclohexanecarboxamide

HRID 1944762Notes

Reaction equation

HRID 1944762 reaction equation
[O:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=2)[N:3]=[CH:2]1.[NH2:16][CH:17]1[CH2:22][CH2:21][C:20]([OH:34])([C:23]([NH:25][CH:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:27])=[O:24])[CH2:19][CH2:18]1.C(N(C(C)C)CC)(C)C>ClCCl>[OH:34][C:20]1([C:23]([NH:25][CH:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH3:27])=[O:24])[CH2:21][CH2:22][CH:17]([NH:16][S:12]([C:9]2[CH:10]=[CH:11][C:6]([C:4]3[N:3]=[CH:2][O:1][CH:5]=3)=[CH:7][CH:8]=2)(=[O:14])=[O:13])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 513419514-(Oxazol-4-yl)benzene-1-sulfonyl chloride2×HCID 582917954-Amino-1-hydroxy-N-(1-phenylethyl)cyclohexanecarboxamide2×

Product 1

HCID 582922201-Hydroxy-4-(4-(oxazol-4-yl)phenylsulfonamido)-N-(1-phenylethyl)cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Oxazol-4-yl-benzenesulfonyl chloride (Intermediate 26, 71.5 mg) was added to solution of 4-amino-1-hydroxy-N-(1-phenylethyl)cyclohexanecarboxamide (Intermediate 92, 70 mg) and diisopropylethylamine (0.103 ml) in dichloromethane (2.7 ml). After 16 hours the reaction was diluted with dichloromethane, rinse once using 1N hydrochloric acid followed by once using saturated aqueous sodium bicarbonate. The organics were dried over sodium sulfate, filtered and concentrate to 126 mg crude solid. The title compound was isolated by preparative basic reverse-phase chromatography to yield two isomeric samples of 1-hydroxy-4-(4-(oxazol-4-yl)phenylsulfonamido)-N-(1-phenylethyl)cyclohexanecarboxamide. Yield 4.5 mg.

Workup

  1. washrinse once
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrate to 126 mg crude solid

Sources & evidence

ORD record
ord-caa412cec31a43de81fa75e70e5cf81c
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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