Hydrochloric Acid → Firategrast

HRID 1454110노트

반응식

HRID 1454110 반응식
[OH-].[Na+].[F:3][C:4]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:5]=1[C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:27]([O:28][CH3:29])=[CH:26][C:25]([CH2:30][O:31][CH2:32][CH3:33])=[CH:24][C:23]=2[O:34][CH3:35])=[CH:18][CH:17]=1)[C:10]([O:12]CC)=[O:11])=[O:7].Cl>O.O1CCCC1>[F:3][C:4]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:5]=1[C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:23]([O:34][CH3:35])=[CH:24][C:25]([CH2:30][O:31][CH2:32][CH3:33])=[CH:26][C:27]=2[O:28][CH3:29])=[CH:20][CH:21]=1)[C:10]([OH:12])=[O:11])=[O:7]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11237832HCID 11237832, 화합물

생성물 1

HCID 9935681Firategrast수율 96%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

To a solution of sodium hydroxide (2.9 g) in water-tetrahydrofuran (317 ml-159 ml) was added ethyl (αS)-α-[(2,6-difluorobenzoyl)amino]-4′-ethoxymethyl-2′,6′-dimethoxy(1,1′-biphenyl)-4-propionate (31.7 g) at 15° C. and the mixture was stirred for 4 hours at the same temperature. After neutralizing with 1N HCl, the organic solvent was removed in vacuo. The aqueous layer was cooled, the crystalline precipitates were collected by filtration and recrystallized from ethanol-water to yield (αS)-α-[(2,6-difluorobenzoyl)amino]-4′-ethoxymethyl-2′,6′-dimethoxy(1,1′-biphenyl)-4-propionic acid (28.8 g).

후처리

  1. customthe organic solvent was removed in vacuo
  2. temperatureThe aqueous layer was cooled
  3. customthe crystalline precipitates
  4. filtrationwere collected by filtration
  5. customrecrystallized from ethanol-water

출처 및 근거

ORD 기록
ord-05dc434d64d34e8fb0320530f58f5fc2
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476758B2

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