HCID 54313272, compound → HCID 54438115, compound

HRID 2351219Notes

Reaction equation

HRID 2351219 reaction equation
[C:1]([O:5][C:6](=[O:47])[CH2:7][N:8]([C:18](=[O:46])[C@H:19]([CH3:45])[NH:20][C@H:21]([C:42]([OH:44])=[O:43])[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][N:29](C(OCC2C=CC=CC=2)=O)[CH2:28][CH2:27]1)[CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[C:1]([O:5][C:6](=[O:47])[CH2:7][N:8]([C:18](=[O:46])[C@H:19]([CH3:45])[NH:20][C@H:21]([C:42]([OH:44])=[O:43])[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]1)[CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 54313272HCID 54313272, compound

Product 1

HCID 54438115HCID 54438115, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 20 ml of methanol is dissolved 0.5 g of N-[N-[(S)-5-(1-benzyloxycarbonyl-4-piperidyl)-1-carboxypentyl]-L-alanyl]-N-(indan-2-yl)glycine tert-butyl ester, and a catalytic reduction is carried out at ambient temperature and under atmospheric pressure using 10% palladium-carbon (50% wet., 0.5 g) as a catalyst. After stirring at room temperature for 4 hours, the catalyst is filtered off, and the filtrate is concentrated under reduced pressure to give 0.28 g of N-[N-[(S)-5-(4-piperidyl)-1-carboxypentyl]-L-alanyl]-N-(indan-2-yl)glycine tert-butyl ester as a colorless powder.

Workup

  1. customis carried out at ambient temperature and under atmospheric pressure
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-e798f8b804ea4837b217232ab7621df9
Source dataset
uspto-grants-1989_10
Patent number
US04871842

Reaction notes

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