Benzyloxyamine hydrochloride → HCID 178461277, compound

HRID 1694462Notes

Reaction equation

HRID 1694462 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-15d2c8446b594a7e9d0e671f640e8e1a
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

Loading…