Water → 5-Chloro-N-[(S)-2-hydroxy-1-(4-hydroxycyclohexyl)ethyl]thiophene-2-sulfonamide
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](NCC(O)=O)=[CH:4][CH:3]=1.[OH2:13].[H][H].[Cl:16][C:17]1[S:21][C:20]([S:22](Cl)(=[O:24])=[O:23])=[CH:19][CH:18]=1.[CH3:26][CH2:27][N:28](CC)CC>[OH-].[Na+].[Ni]>[Cl:16][C:17]1[S:21][C:20]([S:22]([NH:28][C@@H:27]([CH:5]2[CH2:4][CH2:3][CH:2]([OH:1])[CH2:7][CH2:6]2)[CH2:26][OH:13])(=[O:24])=[O:23])=[CH:19][CH:18]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-hydroxy-L-phenylglycine (10 g, 60 mmole) in NaOH (20 mL, 3M) was added water (380 mL) and Raney nickel (30 g). The reaction mixture was hydrogenated at about 3 atm at 60 to 80° C. for 36 h in a hydrogen bomb. The reaction mixture was filtered through Celite and reduced in volume to about 80-100 mL and dioxane (100 mL) was added. The resulting mixture was cooled to 0° C. and treated with Et3N (10 mL) and 5-chlorothiophene-2-sulfonyl chloride (16 g, 72 mmoles). The reaction was allowed to warn up to 25° C. and stirred overnight. The dioxane and Et3N were removed and the remaining aqueous solution diluted with 1N aq. HCl. The resulting precipitate was collected, washed with water and diethyl ether to give the desired product as a white solid (12 g, 50% in two steps) (100% purity by ELSD, m/z=352 (M−1)).
Workup
- filtrationThe reaction mixture was filtered through Celite
- additionwas added
- customto warn up to 25° C.
- customThe dioxane and Et3N were removed
- additionthe remaining aqueous solution diluted with 1N aq. HCl
- customThe resulting precipitate was collected
- washwashed with water and diethyl ether
Sources & evidence
- ORD record
- ord-f41632711cee4680aba870c000269295
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842718B2
Reaction notes
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