Ammonium Hydroxide → HCID 44409047, compound

HRID 2084967Notes

Reaction equation

HRID 2084967 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]#[C:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[CH2:27][CH2:26][S:25][C:24]([CH3:29])([CH3:28])[C@@H:23]2[C:30]([NH:32][OH:33])=[O:31])(=[O:21])=[O:20])=[CH:15][CH:14]=1)(=O)C.[OH-].[NH4+]>CO>[OH:33][NH:32][C:30]([C@H:23]1[C:24]([CH3:28])([CH3:29])[S:25][CH2:26][CH2:27][N:22]1[S:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:10]#[C:9][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])=[CH:14][CH:15]=1)(=[O:21])=[O:20])=[O:31]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 87599656HCID 87599656, compound

Product 1

HCID 44409047HCID 44409047, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.152 g (0.305 mmol) of 7-[4-({(3S)-3-[(hydroxyamino)carbonyl]-2,2-dimethylthiomorpholinyl}sulfonyl)phenoxy]-5-heptynyl acetate, 3 mL of aqueous ammonium hydroxide and 3 mL of methanol was stirred at room temperature for 18 h and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 1.5% methanol/dichloromethane to provide 0.09 g (65%) of (3S)-N-hydroxy-4-({4-[(7-hydroxy-2-heptynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholinecarboxamide as a white solid. Electrospray Mass Spec: 457.0 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with 1.5% methanol/dichloromethane

Sources & evidence

ORD record
ord-422124807f314ff1919b5fe285c62ba2
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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