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

HRID 1793825Notes

Reaction equation

HRID 1793825 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4f9446d7947a4d80a448c1c65dff12fe
Source dataset
uspto-grants-2006_04
Patent number
US07022690B2

Reaction notes

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