Benzyloxyamine hydrochloride → HCID 178461277, compound

HRID 1190014Notes

Reaction equation

HRID 1190014 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]([C:24]([C@H:26]2[CH2:31][CH2:30][C@H:29]([CH3:32])[CH2:28][CH2:27]2)=[O:25])[C:9]2[CH:13]=[C:12]([C:14]3[CH2:19][CH2:18][C:17](=O)[CH2:16][CH:15]=3)[S:11][C:10]=2[C:21]([OH:23])=[O:22])[CH2:4][CH2:3]1.Cl.[CH2:34]([O:41][NH2:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([O-])(=O)C.[Na+]>O.C(O)C>[CH2:34]([O:41][N:42]=[C:17]1[CH2:18][CH2:19][C:14]([C:12]2[S:11][C:10]([C:21]([OH:23])=[O:22])=[C:9]([N:8]([C@H:5]3[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]3)[C:24]([C@H:26]3[CH2:27][CH2:28][C@H:29]([CH3:32])[CH2:30][CH2:31]3)=[O:25])[CH:13]=2)=[CH:15][CH2:16]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium AcetateHCID 178461279HCID 178461279, compound

Product 1

HCID 178461277HCID 178461277, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of 3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(4-oxo-cyclohex-1-enyl)-thiophene-2-carboxylic acid (30 mg, 0.065 mmol) in a 2:1 H2O-ethanol mixture (3 mL) were added O-benzylhydroxylamine hydrochloride (21 mg, 0.13 mmol) and sodium acetate (18 mg, 0.13 mmol), and the mixture was stirred at room temperature overnight. Then the mixture was extracted with CH2Cl2, organic phase was dried over Na2SO4, concentrated under reduced pressure, and purified by column chromatography on silica gel eluting with 2-15% MeOH in CH2Cl2 to give 20 mg (54%) of 5-{4-benzyloxyimino-cyclohex-1-enyl}-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid.

Workup

  1. extractionThen the mixture was extracted with CH2Cl2, organic phase
  2. dry with materialwas dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography on silica gel eluting with 2-15% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-71294d8fd0f5474b92fbd78ddb8e1df0
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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