Triphenylphosphine → (2R)-Methyl 2-(tert-butoxycarbonylamino)-(4-((S)-2-methyl-butoxy)-phenyl)acetate

HRID 454996

반응식

HRID 454996 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C@@H:22]([CH2:25][CH3:26])[CH2:23]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]([CH3:23])[CH2:25][CH3:26])=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 2723602(S)-2-methyl-1-butanolHCID 5363146Diisopropyl azodicarboxylateHCID 10934864Methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-(4-hydroxyphenyl)acetate

생성물 1

HCID 67438449(2R)-Methyl 2-(tert-butoxycarbonylamino)-(4-((S)-2-methyl-butoxy)-phenyl)acetate수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 0° C. solution of (R)-Methyl 2-(tert-butoxycarbonylamino)-2-(4-hydroxyphenyl)acetate (2.8 g, 10 mmol), (S)-2-methyl-1-butanol (1.1 mL, 10 mmol), triphenylphosphine (2.6 g, 10 mmol), and tetrahydrofuran (100 mL) was treated dropwise with diisopropylazodicarboxylate (1.9 mL, 10 mmol) via syringe. The resulting reaction mixture was allowed to warm to room temperature and maintained overnight. The reaction was concentrated and the residue was purified by column chromatography on silica gel (5%-10% ethyl acetate in hexanes) to afford (2R)-Methyl 2-(tert-butoxycarbonylamino)-(4-((S)-2-methyl-butoxy)-phenyl)acetate (2.8 g, 80% yield) as a clear, colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.27 (d, J=7.3 Hz, 2H), 6.88 (d, J=8.6 Hz, 2H), 5.49 (d, J=6.6 Hz, 1H), 5.26 (d, J=7.3 Hz, 1H), 3.81 (dd, J=9.1, 6.1 Hz, 1H), 3.73 (s, 3H), 3.69-3.76 (m, 1H), 1.86 (dq, J=13.1, 6.5 Hz, 1H), 1.52-1.61 (m, 1H), 1.45 (s, 9H), 1.22-1.33 (m, 2H), 1.02 (d, J=6.8 Hz, 3H), 0.95 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 352.2 [(M+H)+, calcd for C19H30NO5 352.5].

후처리

  1. customThe resulting reaction mixture
  2. temperaturemaintained overnight
  3. concentrationThe reaction was concentrated
  4. customthe residue was purified by column chromatography on silica gel (5%-10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-f8b0fafec7b14b4392a99764911949bc
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497271B2

연결된 노트

불러오는 중…