{(3S)-3-[(tert-Butoxycarbonyl)amino]-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl}acetic acid → HCID 53796192, compound

HRID 2418773Notes

Reaction equation

HRID 2418773 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]([CH2:20][C:21]([OH:23])=[O:22])[C:10]1=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Rh]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][CH:13]2[CH2:16][CH2:17][CH2:18][CH2:19][CH:12]2[N:11]([CH2:20][C:21]([OH:23])=[O:22])[C:10]1=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 13604460{(3S)-3-[(tert-Butoxycarbonyl)amino]-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl}acetic acid

Product 1

HCID 53796192HCID 53796192, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(S)-t-butyloxycarbonylamino-1-carboxymethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (5 g) in ethanol (100 ml) was hydrogenated at 45 psi using 5% rhodium on carbon (2 g) as catalyst, until uptake ceased. The catalyst was filtered off (celite) and the solvent removed under pressure to give 3-(S)-t-butyloxycarbonylamino-1-carboxymethyl-2,3,4,5,5a,6,7,8,9,9a-decahydro-1H-[1]benzazepin-2-one which was used without further purification for the next synthetic step.

Workup

  1. filtrationThe catalyst was filtered off (celite)
  2. customthe solvent removed under pressure

Sources & evidence

ORD record
ord-87e1277fa4c94b0cb379401a415ff118
Source dataset
uspto-grants-1984_09
Patent number
US04473575

Reaction notes

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