Diisopropylethylamine → HCID 73128480, compound

HRID 736834Notes

Reaction equation

HRID 736834 reaction equation
[CH3:1][C:2]1([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[C:25]([CH3:33])[CH:24]=3)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O-:10])=O.F[P-](F)(F)(F)(F)F.[N:41]1([O:50][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.NO>CN(C=O)C>[OH:50][NH:41][C:8]([CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1([CH3:1])[NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[C:25]([CH3:33])[CH:24]=2)=[CH:19][CH:20]=1)(=[O:13])=[O:14])=[O:10]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 131727646HCID 131727646, compound

Product 1

HCID 73128480HCID 73128480, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of racemic (1S,2R)-2-methyl-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxylate (0.075 g) in DMF (0.8 mL) was added BOP (0.1 g, 1.3 eq), diisopropylethylamine (0.122 mL, 4 eq) and hydroxylamine hydrochloride (0.024 g, 2 eq). The reaction was stirred for 8 h and purified by direct injection onto an HPLC to afford racemic (1S,2R)-N-hydroxy-2-methyl -2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxamide (0.03 g, 40%) as a white powder. MS: 484.1 (M+H)+

Workup

  1. custompurified by direct injection onto an HPLC

Sources & evidence

ORD record
ord-d1d71042f403443a870f3253daf17156
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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