(2S,3S,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-2-hydroxy-3-phenylpropionate → (2S,4S,5S,alphaS)-2-Ethyl-3-(alpha-methylbenzyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid t-butyl ester

HRID 1637047노트

반응식

HRID 1637047 반응식
[CH2:1]([N:4]([C@@H:21]([CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@@H:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@H:6]([OH:14])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1.[Rh]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:10]([O:9][C:7]([C@H:6]1[O:14][C@@H:1]([CH2:2][CH3:3])[N:4]([C@@H:21]([CH3:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:5]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

참가 물질

4

반응물 1

HCID 86755227(2S,3S,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-2-hydroxy-3-phenylpropionate

생성물 1

HCID 86755235(2S,4S,5S,alphaS)-2-Ethyl-3-(alpha-methylbenzyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid t-butyl ester수율 83%

시약·촉매·용매 2

HCID 178479813HCID 178479813, 화합물촉매HCID 1140Toluene용매2회

실험 절차

To a solution of compound (27) from Example 12 (1.039 g, 2.73 mmol) in anhydrous toluene (25 ml) was added tris(triphenylphosphine) rhodium(I) chloride (126 mg, 5 mol %). This solution was refluxed for 4 hours whereafter the toluene was removed under reduced pressure. The residue was treated with diethyl ether, precipitating the catalyst, and the solution was passed through alumina grade 5. After removal of the solvent under reduced pressure, the resulting oil was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:19)] affording the title compound (Rf 0.40) as a colourless oil (0.86 g, 83%). δH (300 MHz; CDCl3) 7.33-7.18 (10H, m, Ph), 4.48 (1H, t, NCHO), 4.38 (1H, d, J=8.0, PhCHCH), 4.21 (1H, d, J=8.0, PhCHCH), 4.01 (1H, q, J=6.9, PhCHCH3), 1.91 (2H, m, CHCH2CH3), 1.27 (3H, d, J=6.9, PhCHCH3), 1.15 (3H, t, J=7.5, CHCH2CH3), 0.99 (9H, s, (CH3)3C).

후처리

  1. customwas removed under reduced pressure
  2. additionThe residue was treated with diethyl ether
  3. customprecipitating the catalyst
  4. customAfter removal of the solvent under reduced pressure
  5. customthe resulting oil was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:19)]

출처 및 근거

ORD 기록
ord-ad151db2dfb64c179edb4f15a00b19e2
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06037498

반응 노트

불러오는 중…