Oxalyl chloride → (trans)-N-Hydroxy-2-[(4-Phenoxybenzenesulfonyl)amino]cyclohexane-carboxamide

HRID 1091963Notes

Reaction equation

HRID 1091963 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[C:24]([OH:26])=O)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[O:35][NH2:36]>>[OH:35][NH:36][C:24]([C@@H:19]1[CH2:20][CH2:21][CH2:22][CH2:23][C@H:18]1[NH:17][S:14]([C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1)(=[O:16])=[O:15])=[O:26]

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 66588486(trans)-2-[(4-Phenoxybenzenesulfonyl)amino]cyclohexanecarboxylic acid

Product 1

HCID 86625607(trans)-N-Hydroxy-2-[(4-Phenoxybenzenesulfonyl)amino]cyclohexane-carboxamideYield 46.2%

Procedure

A solution of the acid obtained in Example 7 (1.00 g, 2.66 mmol) was reacted with oxalyl chloride (2M solution in CH2Cl2, 6.65 mL, 13.3 mmol) followed by O-(trimethylsilyl)hydroxylamine (2.8 g, 26.64 mmol) as described in Example 2 to obtain 0.48 g (46%) of the desired product. The melting point was 182-184° C. Mass spectrometry revealed a molecular ion (MH)+ peak at m/z 391. Proton NMR analysis in CDCl3 resulted in the following chemical shifts (δ): 0.98-1.96 (m, 8H, cyclohexyl methylenes), 2.05-2.16 (m, 1H, C-1H), 3.50-3.67 (broad hump, 1H, C-2H), 6.15 (broad hump, 1H, SO2NH), 7.01-7.88 (m, 9H, aryl-H), and 8.98 (broad s, 1H, CONH).

Sources & evidence

ORD record
ord-d88c5d4a4d0c4d0bb158eaf077d33a1a
Source dataset
uspto-grants-2012_03
Patent number
US08129406B2

Reaction notes

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