Hydroxylamine → HCID 86608548, compound
Reaction equation
C[O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:12][CH:11]=1.NO.[OH-].[K+].CO>C1COCC1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([S:17]([NH:16][C:13]2[CH:14]=[CH:15][C:10]([S:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:27])=[O:2])=[CH:11][CH:12]=2)(=[O:18])=[O:19])=[CH:25][CH:24]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the 6-(4-(4-chlorobenzenesulfonylamino)-phenylsulfanyl)-hexanoic acid methyl ester (300 mg, 0.7 mmol) in distilled THF (10 mL) containing 50% aqueous hydroxylamine (0.4 mL, 6.3 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (1.2 mL, 1M, 1.2 mmol) in a dropwise manner. After stirring at 0° C. for 1 h, distilled water (10 mL) was added and the mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C. The aqueous solution was extracted with ethyl acetate (2×15 mL) and the combined extracts were washed with brine (15 mL), dried over anhydrous MgSO4, filtered and evaporated to dryness. The solid residue was recrystallised from ethyl acetate/diethyl ether to give the title compound (200 mg, 66%) as a white powder, mp 160-163° C.
Workup
- distillationdistilled water (10 mL)
- additionwas added
- additionthe mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C
- extractionThe aqueous solution was extracted with ethyl acetate (2×15 mL)
- washthe combined extracts were washed with brine (15 mL)
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- customevaporated to dryness
- customThe solid residue was recrystallised from ethyl acetate/diethyl ether
Sources & evidence
- ORD record
- ord-d19bff90213342468dc240a197016260
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683185B2
Reaction notes
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