3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-5-acetoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one → 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

HRID 482746Notes

Reaction equation

HRID 482746 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH:14](OC(=O)C)[C:13]2[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=2[N:11]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:10]1=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][C:13]2[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=2[N:11]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:10]1=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 132435333-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-5-acetoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

Product 1

HCID 132435313-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-5-acetoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (2.2 g) in ethanol (300 ml) containing 10% Pd/C (2.0 g) was placed in a pressure bottle and hydrogenated at 3 atmospheres pressure and 70° for 3 days. The catalyst was filtered off and the filtrate evaporated to give 3-(S)-t-butyloxycarbonylamino-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 164°-165° [α]D =-200.6° (c=0.64 in DMF).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-9b0dc71656b34940a4b67150aa91ced8
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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