HCID 131714800, compound → HCID 18603968, compound

HRID 364062Notes

Reaction equation

HRID 364062 reaction equation
[C:1]([NH:9][CH:10]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40]CC2C=CC=CC=2)=[CH:36][CH:35]=1)[CH:11]([OH:32])[CH2:12][N:13]([CH3:31])[C:14]([N:16]1[CH2:30][CH2:29][CH2:28][C@H:17]1[C:18]([O:20]CC1C=CC=CC=1)=[O:19])=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO>[C:1]([NH:9][CH:10]([CH2:33][C:34]1[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=1)[CH:11]([OH:32])[CH2:12][N:13]([CH3:31])[C:14]([N:16]1[CH2:30][CH2:29][CH2:28][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

Participants

4

Reactant 1

HCID 131714800HCID 131714800, compound

Product 1

HCID 18603968HCID 18603968, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The ester product from part (c) is taken up into 125 ml. of methanol containing 400 mg. of palladium on carbon catalyst (10%) and stirred under positive hydrogen pressure for 20 hours. The reaction mixture is filtered and concentrated to dryness in vacuo. The crude product is purified chromatographically to yield (±)-1-[[[3-(benzoylamino)-4-(4-hydroxyphenyl)-2-hydroxybutyl]methylamino]carbonyl]-L-proline.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated to dryness in vacuo
  3. customThe crude product is purified chromatographically

Sources & evidence

ORD record
ord-412d1f5de2484652ae4253911dd0fb57
Source dataset
uspto-grants-1986_08
Patent number
US04604402

Reaction notes

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