(Z)-1-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-3-methoxy-3-oxoprop-1-en-2-yl benzoate → (R)-3-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

HRID 132439노트

반응식

HRID 132439 반응식
[C:1]([O:9]/[C:10](/[C:32]([O:34][CH3:35])=[O:33])=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:14]([CH3:26])[C:13]=1[CH2:27][O:28][C:29](=[O:31])[CH3:30])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>ClCCl.[B-](F)(F)(F)F.CC[C@H]1P(C2C(P3[C@H](CC)CC[C@H]3CC)=CC=CC=2)[C@H](CC)CC1.C1[CH][CH]CC[CH][CH]C1.[Rh]>[C:1]([O:9][C@H:10]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])=[C:14]([CH3:26])[C:13]=1[CH2:27][O:28][C:29](=[O:31])[CH3:30])[C:32]([O:34][CH3:35])=[O:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 59732069(Z)-1-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-3-methoxy-3-oxoprop-1-en-2-yl benzoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 59732072(R)-3-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

시약·촉매·용매 2

HCID 11549211CID 11549211촉매HCID 6344Dichloromethane용매

실험 절차

(Z)-1-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-3-methoxy-3-oxoprop-1-en-2-yl benzoate (20.00 g, 41.4 mmol) in dichloromethane (120.00 ml) was added (−)-1,2-bis((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I)tetrafluoroborate (280.00 mg, 0.424 mmol) under nitrogen atmosphere. The reaction mixture was hydrogenated at 60 psi pressure of hydrogen for 12h. The solvent was removed and crude product was carried to the next step as such. MS (ESI) 508 (M+H); Rf=2.53.

후처리

  1. customThe solvent was removed

출처 및 근거

ORD 기록
ord-8fa164879af04b39828fbffe1f1ae5f7
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384931B2

반응 노트

불러오는 중…