Hydrochloric Acid → HCID 131714803, compound

HRID 364065Notes

Reaction equation

HRID 364065 reaction equation
[C:1]([NH:9][CH:10]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:11]([OH:46])[CH2:12][N:13]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35]C(OCC1C=CC=CC=1)=O)[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.[ClH:54]>[Pd].C(O)C>[ClH:54].[NH2:35][CH2:34][CH2:33][CH2:32][CH2:31][N:13]([CH2:12][CH:11]([OH:46])[CH:10]([NH:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:14]([N:16]1[CH2:30][CH2:29][CH2:28][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131714801HCID 131714801, compound

Product 1

HCID 131714803HCID 131714803, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The ester product from part (g) is taken into 40 ml. of 95% ethanol, 0.584 ml. of 1N hydrochloric acid, and 50 mg. of palladium on carbon catalyst (10%). The mixture is stirred under hydrogen pressure for 24 hours. The reaction mixture is then filtered and concentrated to dryness in vacuo. The crude product is purified on an LH-20 column in water to yield 1-[[(4-aminobutyl)[3-(benzoylamino)-2-hydroxy-4-phenylbutyl]amino]carbonyl]-L-proline, monohydrochloride.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated to dryness in vacuo
  3. customThe crude product is purified on an LH-20 column in water

Sources & evidence

ORD record
ord-7fd3d841d7014245808213cddc22f155
Source dataset
uspto-grants-1986_08
Patent number
US04604402

Reaction notes

Loading…