Water → 5-Chloro-N-[(S)-2-hydroxy-1-(4-hydroxycyclohexyl)ethyl]thiophene-2-sulfonamide

HRID 398273

반응식

HRID 398273 반응식
[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]=1

참가 물질

8

반응물 5

HCID 962WaterHCID 8471TriethylamineHCID 67149N-(4-Hydroxyphenyl)glycineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 590861855-Chloro-N-[(S)-2-hydroxy-1-(4-hydroxycyclohexyl)ethyl]thiophene-2-sulfonamide

시약·촉매·용매 2

HCID 935Nickel촉매HCID 14798Sodium Hydroxide용매

반응 조건

온도
0 °C

실험 절차

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 warm 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)).

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. additionwas added
  3. temperatureto warm up to 25° C.
  4. customThe dioxane and Et3N were removed
  5. additionthe remaining aqueous solution diluted with 1N aq. HCl
  6. customThe resulting precipitate was collected
  7. washwashed with water and diethyl ether

출처 및 근거

ORD 기록
ord-14d8f51c5c6e4961864a90bb7cf32a45
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610734B2

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