2-(4-Acetylbenzenesulfonamido)acetic acid → {4-[3E-(2,4-Dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]benzenesulfonylamino}acetic acid

HRID 347379

반응식

HRID 347379 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][C:15]([OH:17])=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:18][O:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:24][C:21]=1[CH:22]=O.C[O-].[Li+]>CN(C=O)C.CO>[CH3:18][O:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:24][C:21]=1/[CH:22]=[CH:2]/[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][C:15]([OH:17])=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1)=[O:3]

참가 물질

6

반응물 3

HCID 21201292-(4-Acetylbenzenesulfonamido)acetic acidHCID 4177230Lithium methanolateHCID 210825102,4-Dimethoxy-5-pyrrolidin-1-ylbenzaldehyde

생성물 1

HCID 11178975{4-[3E-(2,4-Dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]benzenesulfonylamino}acetic acid수율 8%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A solution of (4-acetylbenzenesulfonylamino)acetic acid (Ex-26A, 226 mg, 0.878 mmol) and 2,4-dimethoxy-5-pyrrolidin-1-ylbenzaldehyde (Ex-38B, 216 mg, 0.922 mmol) in DMF (8.0 mL) and MeOH (3.6 mL) was treated with lithium methoxide (140 mg, 3.69 mmol) and stirred for 21 h at room temperature under nitrogen. The reaction mixture was quenched with water (10 mL) and extracted ethyl acetate (2×20 mL). The aqueous phase was acidified with 6N HCl to pH3 and was extracted with (3:1) ethyl acetate/THF (6×25 mL). The organic phase was brined, dried over sodium sulfate, and concentrated to a red solid. Precipitation from dichloromethane (5 mL) gave the title compound (33 mg, 8%) as a brown solid, mp 155–158° C. 1H-NMR (300 MHz, DMSO-d6) 12.06 (br s, 1), 8.22 (m, 3H), 8.04 (d, 1H, J=15.3 Hz), 7.89 (d, 2H, J=7.8 Hz), 7.64 (d, 1H, J=15.3 Hz), 7.18 (s, 1H), 6.67 (s, 1H), 3.86 (s, 6H), 3.29 (br s, 2H), 3.16 (br s, 4H), 1.82 (br s, 4H). HRMS (ESI) Calcd. for C23H26N2O7S: 475.1539 [(M+H)+]; Found: 475.1547.

후처리

  1. customThe reaction mixture was quenched with water (10 mL)
  2. extractionextracted ethyl acetate (2×20 mL)
  3. extractionwas extracted with (3:1) ethyl acetate/THF (6×25 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a red solid
  6. customPrecipitation from dichloromethane (5 mL)

출처 및 근거

ORD 기록
ord-2b14188aee194d1394e6f177d7d71b63
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173129B2

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