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Dicyclohexylcarbodiimide → 3-Benzylpyrrolylmethyl 2-(5-fluoro-2-benzothienyl)-3-methylbutanoate

HRID 27943
Notes
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Reaction equation

HRID 27943 reaction equation
[CH2:1]([C:8]1[CH:12]=[CH:11][NH:10][C:9]=1[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:17]=[CH:18][C:19]2[S:23][C:22]([CH:24]([CH:28]([CH3:30])[CH3:29])[C:25](O)=[O:26])=[CH:21][C:20]=2[CH:31]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl.CN(C=O)C>[F:15][C:16]1[CH:17]=[CH:18][C:19]2[S:23][C:22]([CH:24]([CH:28]([CH3:29])[CH3:30])[C:25]([O:14][CH2:13][C:9]3[NH:10][CH:11]=[CH:12][C:8]=3[CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:26])=[CH:21][C:20]=2[CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 537232412-(5-Fluoro-2-benzothienyl)-3-methylbutanoic acidHCID 543430813-Benzyl-1-pyrrolylmethanol

Product 1

HCID 537530013-Benzylpyrrolylmethyl 2-(5-fluoro-2-benzothienyl)-3-methylbutanoate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-benzylpyrrolyl methanol (1.8 mmol), 2-(5-fluoro-2-benzothienyl)-3-methylbutanoic acid (2.0 mmol) and 4-dimethylaminopyridine (2.0 mmol) in 20 ml of methylene chloride and 2 ml of DMF is added N,N'-dicyclohexylcarbodiimide (2.0 mml). The reaction mixture is stirred, under nitrogen, for about two hours and then filtered and extracted with water. The aqueous phase is extracted with ether. The combined organic phases are washed with saturated aqueous NaHCO3, water and saturated aqueous NaCl, dried over CaSO4 and solvent evaporated to yield 3-benzylpyrrolylmethyl 2-(5-fluoro-2-benzothienyl)-3-methylbutanoate.

Workup

  1. filtrationfiltered
  2. extractionextracted with water
  3. extractionThe aqueous phase is extracted with ether
  4. washThe combined organic phases are washed with saturated aqueous NaHCO3, water and saturated aqueous NaCl
  5. dry with materialdried over CaSO4 and solvent
  6. customevaporated

Sources & evidence

ORD record
ord-b306f7b542d648819f0f1e38cfa67467
Source dataset
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04224330

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes