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

HRID 1793825ノート

反応式

HRID 1793825 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4f9446d7947a4d80a448c1c65dff12fe
出典データセット
uspto-grants-2006_04
特許番号
US07022690B2

反応ノート

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