HCID 86739671, compound → HCID 70493469, compound

HRID 1632178Notes

Reaction equation

HRID 1632178 reaction equation
[C:1]([NH:9][CH:10]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH:11]([OH:33])[CH2:12][NH:13][C@H:14]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:21][C:22]([O:24]CC2C=CC=CC=2)=[O:23])[C:15]1=[O:32])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[C:1]([NH:9][CH:10]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH:11]([OH:33])[CH2:12][NH:13][C@H:14]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:21][C:22]([OH:24])=[O:23])[C:15]1=[O:32])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86739671HCID 86739671, compound

Product 1

HCID 70493469HCID 70493469, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the phenylmethyl ester product from part (a) (2.0 mmole) in 95% ethanol (50 ml.) containing 10% palladium on carbon catalyst (0.2 g.) is hydrogenated under atmospheric pressure overnight. The catalyst is filtered, washed with 95% ethanol and the filtrate concentrated under reduced pressure into an oily residue which is then treated for 5 minutes with 1.4N hydrochloric acid/acetic acid (10 ml.). The reaction mixture is concentrated under reduced pressure to yield a solid residue. The crude product is purified on an HP-20 column (5% methanol/0.01N hydrochloric acid→90% methanol/0.01N hydrochloric acid) to give (S)-3-[[3-(benzoylamino)-2-hydroxy-4-phenylbutyl]amino]-hexahydro-2-oxo-1H-azepine-1-acetic acid.

Workup

  1. customis hydrogenated under atmospheric pressure overnight
  2. filtrationThe catalyst is filtered
  3. washwashed with 95% ethanol
  4. concentrationthe filtrate concentrated under reduced pressure into an oily residue which
  5. additionis then treated for 5 minutes with 1.4N hydrochloric acid/acetic acid (10 ml.)
  6. concentrationThe reaction mixture is concentrated under reduced pressure
  7. customto yield a solid residue
  8. customThe crude product is purified on an HP-20 column (5% methanol/0.01N hydrochloric acid→90% methanol/0.01N hydrochloric acid)

Sources & evidence

ORD record
ord-f03d53657d11439d9d8adb28db197dfc
Source dataset
uspto-grants-1984_10
Patent number
US04474778

Reaction notes

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