Triethylamine → Phenylmethyl gamma-oxo-alpha-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoate

HRID 362468Notes

Reaction equation

HRID 362468 reaction equation
S(Cl)(Cl)=O.[C:5]([CH2:8][CH:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])([OH:7])=O.FC(F)(F)C(O)=O.[CH:34]1[S:35][CH:36]=[C:37]2[CH2:41][NH:40][CH2:39][C:38]=12.C(N(CC)CC)C>ClCCl.CN(C)C=O.O>[O:7]=[C:5]([N:40]1[CH2:39][C:38]2=[CH:34][S:35][CH:36]=[C:37]2[CH2:41]1)[CH2:8][CH:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 14213080HCID 14213080, compoundHCID 675736455,6-dihydro-4H-thieno[3,4-c]pyrrole trifluoroacetate

Product 1

HCID 15337444Phenylmethyl gamma-oxo-alpha-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoateYield 37.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.49 ml (6.8 mmol) of thionyl chloride is added, at 0° C., to a solution of 1.01 g (3.4 mmol) of phenylmethyl 3-carboxy-2-(phenylmethyl)-1-propanoate in 15 ml of dichloromethane, followed by two drops of N,N-dimethylformamide. After 2 h at room temperature, the mixture is evaporated to dryness and the residue is dissolved in 25 ml of dichloromethane. The solution is cooled to 0° C. and then a solution of 0.81 g (3.4 mmol) of 5,6-dihydro-4H-thieno[3,4-c]pyrrole trifluoroacetate and 1.42 ml (10.2 mmol) of triethylamine in 25 ml of dichloromethane is added. After 16 h at room temperature, 25 ml of water are added, and the organic phase is decanted off, washed with a saturated sodium chloride solution and then dried over sodium sulphate and evaporated to dryness. The residue is chromatographed on a silica gel with the aid of the eluent mixture ethyl acetate/hexane 3/7. 0.52 g of a white solid is obtained.

Workup

  1. customthe mixture is evaporated to dryness
  2. dissolutionthe residue is dissolved in 25 ml of dichloromethane
  3. waitAfter 16 h at room temperature
  4. customthe organic phase is decanted off
  5. washwashed with a saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness
  8. customThe residue is chromatographed on a silica gel with the aid of the eluent mixture ethyl acetate/hexane 3/7

Sources & evidence

ORD record
ord-f9409d19cff14e35adf5eda0e54eebdb
Source dataset
uspto-grants-1999_02
Patent number
US05869518

Reaction notes

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