Triphenylphosphine → 17-Ethyl-1-hydroxy-12-[2'-(4"-amino-3"-propyloxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

HRID 248278노트

반응식

HRID 248278 반응식
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:57])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([N:50]=[N+]=[N-])[CH:46]([O:53][CH2:54][CH2:55][CH3:56])[CH2:45]2)[CH:7]([CH3:58])[CH2:6][CH2:5][C:4]1=[O:59])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[OH-:9].[NH4+:16].[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:57])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([NH2:50])[CH:46]([O:53][CH2:54][CH2:55][CH3:56])[CH2:45]2)[CH:7]([CH3:58])[CH2:6][CH2:5][C:4]1=[O:59])[CH3:2]

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 5709641317-Ethyl-1-hydroxy-12-[2'-(4"-azido-3"-propyloxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

생성물 2

HCID 14923Ammonium Hydroxide수율 2%HCID 5699537717-Ethyl-1-hydroxy-12-[2'-(4"-amino-3"-propyloxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone수율 166.1%

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
70 °C

실험 절차

To a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-azido-3"-propyloxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (46 mg) in 10% aqueous benzene (900 μl) was added triphenylphosphine (29 mg) and the mixture heated to 70° C. with stirring. After 6.5 hours, the stir bar was removed and the reaction cooled to room temperature. The mixture was concentrated to 10% volume in vacuo and applied directly to a column of silica gel for purification by flash chromatography (ethyl acetate: hexane (1:1)+1% methanol then 2% ammonium hydroxide, 5% methanol in methylene chloride) to give the title compound (37 mg).

후처리

  1. customthe stir bar was removed
  2. temperaturethe reaction cooled to room temperature
  3. concentrationThe mixture was concentrated to 10% volume in vacuo
  4. customapplied directly to a column of silica gel for purification by flash chromatography (ethyl acetate: hexane (1:1)+1% methanol

출처 및 근거

ORD 기록
ord-7885dd5a0dc041bd9c8842c62542382b
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208228

반응 노트

불러오는 중…