Ethanol → HCID 22841466, compound

HRID 1382622Notes

Reaction equation

HRID 1382622 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:45]([OH:47])=[O:46])[CH2:13][CH2:14][C:15]([NH:17][CH2:18][CH2:19][O:20][CH2:21][C:22]1[NH:23][C:24]([CH3:44])=[C:25]([C:40]([O:42][CH3:43])=[O:41])[CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])[C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:48](O)[CH3:49].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:13][CH2:14][C:15]([NH:17][CH2:18][CH2:19][O:20][CH2:21][C:22]1[NH:23][C:24]([CH3:44])=[C:25]([C:40]([O:42][CH3:43])=[O:41])[CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])[C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 22841465HCID 22841465, compound

Product 1

HCID 22841466HCID 22841466, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-(-(S)-4-benzyloxycarbonylamino-4-carboxybutanamido)ethoxymethyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (1.0 g), ethanol (0.27 g), N,N'-dicyclohexylcarbodiimide ("DCCD") (0.34 g) and 4-dimethylaminopyridine (50 mg) was stirred in dichloromethane (10 ml) at room temperature for 18 hours. The resulting N,N'-dicyclohexylurea was then removed by filtration and the filtrate evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0→2% methanol as the eluant. Appropriate fractions were combined and evaporated to give 2-[2-(-(S)-4-benzyloxycarbonylamino-4-ethoxycarbonylbutanamido)ethoxymethyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (0.85 g) as an essentially pure oil.

Workup

  1. customThe resulting N,N'-dicyclohexylurea was then removed by filtration
  2. customthe filtrate evaporated
  3. customThe residue was purified by chromatography on silica
  4. customevaporated

Sources & evidence

ORD record
ord-9a248e37e96b46c28c28cfcab40ff02d
Source dataset
uspto-grants-1989_02
Patent number
US04806557

Reaction notes

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