Allyl iodide → 2-Allyl-3-(4-methoxy-benzenesulfonylamino)-succinic Acid 1-benzyl Ester 4-tert-butyl Ester

HRID 1793824Notes

Reaction equation

HRID 1793824 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([O:15][C:16](=[O:41])[CH:17]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])([CH3:14])([CH3:13])[CH3:12].[CH2:42](I)[CH:43]=[CH2:44]>O1CCCC1>[C:11]([O:15][C:16](=[O:41])[CH:17]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH:18]([CH2:44][CH:43]=[CH2:42])[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])([CH3:13])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 120878632-(4-Methoxy-benzenesulfonylamino)-succinic Acid 4-benzyl Ester 1-tert-butyl Ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-40 °C

Procedure

100 ml dry Tetrahydrofuran (THF) are cooled to −78° C. 1M THF-solution of Lithium bis(trimethylsilyl)amide (47.35 ml, 47.35 mmol) are added while the temperature is maintained. 2-(4-Methoxy-benzenesulfonylamino)-succinic acid 4-benzyl ester 1-tert-butyl ester (10.1 g, 22.5 mmol) are dissolved in 45 ml THF and added dropwise to the reaction solution. The reaction mixture is allowed to stir for 1 h and then warmed briefly to −40° C. After re-cooling to −78° C. Allyliodide (3.1 ml, 33.8 mmol) dissolved in 30 ml THF are added drop-wise. The reaction mixture is allowed to warm to −40° C. and is quenched with a NH4Cl-solution. The organic phase is separated dried over MgSO4 and filtered. The solvent is evaporated and the product is purified with a short flash-chromatography column. Hexane/Ethylacetate (9:1): Cal. 489.6 Found. (M)+ 490.

Workup

  1. temperatureis maintained
  2. additionadded dropwise to the reaction solution
  3. temperatureAfter re-cooling to −78° C
  4. additionare added drop-wise
  5. temperatureto warm to −40° C.
  6. customis quenched with a NH4Cl-solution
  7. customThe organic phase is separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe solvent is evaporated
  11. customthe product is purified with a short flash-chromatography column

Sources & evidence

ORD record
ord-0b4bf61d67084c93a2c903a9e7aa5117
Source dataset
uspto-grants-2006_04
Patent number
US07022690B2

Reaction notes

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