Allyl Alcohol → 2-Allyl-3-(allyl-(4-methoxy-benzenesulfonyl)-amino)-succinic acid 1-benzyl ester 4-tert-butyl ester

HRID 1793825노트

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HRID 1793825 반응식
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=CC=C[CH:2]=1.C(O)C=C.[C:24]([O:28][C:29](=[O:57])[CH:30]([NH:45][S:46]([C:49]1[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=1)(=[O:48])=[O:47])[CH:31]([CH2:42][CH:43]=[CH2:44])[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])([CH3:27])([CH3:26])[CH3:25]>O1CCCC1>[C:24]([O:28][C:29](=[O:57])[CH:30]([N:45]([CH2:6][CH:1]=[CH2:2])[S:46]([C:49]1[CH:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=1)(=[O:48])=[O:47])[CH:31]([CH2:42][CH:43]=[CH2:44])[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])([CH3:27])([CH3:25])[CH3:26]

참가 물질

5

반응물 3

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 120878642-Allyl-3-(4-methoxy-benzenesulfonylamino)-succinic Acid 1-benzyl Ester 4-tert-butyl Ester

생성물 1

HCID 120878652-Allyl-3-(allyl-(4-methoxy-benzenesulfonyl)-amino)-succinic acid 1-benzyl ester 4-tert-butyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Triphenylphosphine (1 g, 3.9 mmol) are solved in 60 ml Tetrahydrofuran (THF) and cooled to 0° C. Diazopropyl dicarboxylate (DIAD) (0.77 ml, 3.9 mmol) are added via syringe and the reaction mixture is stirred for 30 min. Allyl alcohol (16 μl, 0.23 mmol) is added to the yellow suspension and then after 10 min., 2-Allyl-3-(4-methoxy-benzenesulfonylamino)-succinic acid 1-benzyl ester 4-tert-butyl ester (1.4 g, 2.6 mmol) is added. The reaction mixture is stirred for 30 min. at 0° C. and is then allowed to warm to room temp. After evaporation of most of the THF and flash-chromatography with Hexane/Ethylacetate (2:1) the desired product is obtained: 1H NMR (CDCl3 400 MHz), ppm: 7.80 (d, 2H), 7.38 (m, 5H), 6.95 (d, 2H), 5.75 (m, 2H), 5.10 (m, 6H), 3.95 (m, 2H), 3.90 (s, 3H), 3.21 (ddd, 1H), 2.50 (ddd, 1H), 2.35 (ddd, 1H), 1.40 (s, 9H).

후처리

  1. waitafter 10 min.
  2. stirringThe reaction mixture is stirred for 30 min. at 0° C.
  3. temperatureto warm to room temp
  4. customAfter evaporation of most of the THF and flash-chromatography with Hexane/Ethylacetate (2:1) the desired product
  5. customis obtained

출처 및 근거

ORD 기록
ord-4f9446d7947a4d80a448c1c65dff12fe
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022690B2

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