Hydroxyamine hydrochloride → tert-butyl N-[(2R,3S)-3-[[3-benzamido-5-[(E)-N-hydroxy-C-methylcarbonimidoyl]benzoyl]amino]-4-(3,5-difluorophenyl)-2-hydroxybutyl]-N-[(3-methoxyphenyl)methyl]carbamate

HRID 1454189Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:49]=[CH:50][CH:51]=1)[CH2:6][N:7]([CH2:15][C@@H:16]([OH:48])[C@@H:17]([NH:27][C:28](=[O:47])[C:29]1[CH:34]=[C:33]([NH:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:32]=[C:31]([C:44](=O)[CH3:45])[CH:30]=1)[CH2:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=1)[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].Cl.[OH:53][NH2:54]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:49]=[CH:50][CH:51]=1)[CH2:6][N:7]([CH2:15][C@@H:16]([OH:48])[C@@H:17]([NH:27][C:28](=[O:47])[C:29]1[CH:30]=[C:31](/[C:44](=[N:54]/[OH:53])/[CH3:45])[CH:32]=[C:33]([NH:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:34]=1)[CH2:18][C:19]1[CH:20]=[C:21]([F:26])[CH:22]=[C:23]([F:25])[CH:24]=1)[C:8](=[O:14])[O:9][C:10]([CH3:12])([CH3:11])[CH3:13]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl 3-methoxybenzyl((2R,3S)-3-(3-acetyl-5-(benzamido)benzamido)-4-(3,5-difluorophenyl)-2-hydroxybutyl)carbamate (20 mg, 0.0282 mmol) and hydroxyamine hydrochloride (0.0564 mmol) in ethanol (0.14 mL) was heated at 80° C. for 2 h. The reaction mixture was purified by reverse phase prep HPLC to give the title compound (10 mg): HPLC retention time: 2.255 min (method A). MS (ESI) (M+H)+ 725.53.

Workup

customThe reaction mixture was purified by reverse phase prep HPLC

Sources & evidence

ORD record: ord-539b50291e584e1697d0b537b70ce473
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476764B2

Reaction notes

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