3-Pyridinemethanol → HCID 56623210, compound

HRID 364066Notes

Reaction equation

HRID 364066 reaction equation
[C:1]([NH:9][C@@H:10]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:11]([OH:25])[CH2:12][N:13]([CH3:24])[C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39]O)[CH:34]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.O1CCCC1>[C:1]([NH:9][C@@H:10]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH:11]([OH:25])[CH2:12][N:13]([CH3:24])[C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([O:20][CH2:39][C:35]1[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=1)=[O:19])=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 75103-PyridinemethanolHCID 10868DicyclohexylcarbodiimideHCID 13657310HCID 13657310, compound

Product 1

HCID 56623210HCID 56623210, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-[[[(3S)-3-(Benzoylamino)-2-hydroxy-4-phenylbutyl]methylamino]carbonyl]-L-proline (isomer A), 4-dimethylamino pyridine, 3-pyridinylcarbinol and dicyclohexylcarbodiimide are taken up into tetrahydrofuran with stirring in an ice bath. The reaction proceeds overnight at room temperature. The dicyclohexylurea is filtered off and the filtrate is concentrated to dryness. The crude product is chromatographed on silica gel to give 1-[[[(3S)-3-(benzoylamino)-2-hydroxy-4-phenylbutyl]methylamino]carbonyl]-L-proline, 3-pyridinylmethyl ester (isomer A).

Workup

  1. filtrationThe dicyclohexylurea is filtered off
  2. concentrationthe filtrate is concentrated to dryness
  3. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-2d618b811cb24c9295a0a57b3c00205c
Source dataset
uspto-grants-1986_08
Patent number
US04604402

Reaction notes

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