HCID 23335145, compound → 3-Benzylpyrrolylmethyl 2-(6-chloro-2-benzothienyl)-3-methylbutanoate

HRID 27945Notes

Reaction equation

HRID 27945 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6]=[C:7]([CH:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])[S:8][C:4]=2[CH:3]=1.CS(O[CH2:23][C:24]1[NH:25][CH:26]=[CH:27][C:28]=1[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=O)=O>C1COCC1.CN(C=O)C.CCOCC>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6]=[C:7]([CH:9]([CH:13]([CH3:14])[CH3:15])[C:10]([O:12][CH2:23][C:24]3[NH:25][CH:26]=[CH:27][C:28]=3[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:11])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 23335145HCID 23335145, compoundHCID 544831182-(6-Chloro-2-benzothienyl)-3-methylbutanoic acid

Product 1

HCID 538379543-Benzylpyrrolylmethyl 2-(6-chloro-2-benzothienyl)-3-methylbutanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent2×

Procedure

2-(6-Chloro-2-benzothienyl)-3-methylbutanoic acid (3.40 mmol) is stirred together with 0.34 g (3.40 mmol) KHCO3 in 10 ml THF/DMF (1:1) for 15 minutes. Then 3.40 mmol of 3-benzylpyrrolylmethyl methanesulfonate in 5 ml THF/DMF (1:1) is added and the mixture stirred for approximately 48 hours. The reaction is diluted with ether, washed with water (3×) and sat. NaCl, dried and solvent is removed to yield 3-benzylpyrrolylmethyl 2-(6-chloro-2-benzothienyl)-3-methylbutanoate.

Workup

  1. washwashed with water (3×) and sat. NaCl
  2. customdried
  3. customsolvent is removed

Sources & evidence

ORD record
ord-da9b10f718494464b4a8070d2fda862c
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Reaction notes

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