HCID 53783606, compound → HCID 53905807, compound

HRID 280963Notes

Reaction equation

HRID 280963 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([NH:27][C@@H:28]2[C:34](=[O:35])[N:33]([CH2:36][C:37]([O:39]CC3C=CC=CC=3)=[O:38])[C:32]3[CH:47]=[CH:48][CH:49]=[CH:50][C:31]=3[O:30][CH2:29]2)[C:22]([O:24]CC)=[O:23])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[C:22]([C@@H:21]([NH:27][C@@H:28]1[C:34](=[O:35])[N:33]([CH2:36][C:37]([OH:39])=[O:38])[C:32]2[CH:47]=[CH:48][CH:49]=[CH:50][C:31]=2[O:30][CH2:29]1)[CH2:20][CH2:19][CH2:18][CH2:17][CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([OH:24])=[O:23]

Participants

4

Reactant 1

HCID 53783606HCID 53783606, compound

Product 1

HCID 53905807HCID 53905807, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl 3(S)-[5-(1-benzyloxycarbonyl-4-piperidyl)-1(S)-ethoxycarbonylpentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.65 g) in ethanol (40 ml) is subjected to catalytic hydrogenolysis over 10% palladium carbon (1 g, 50% wet) at ambient temperature and pressure until the absorption of hydrogen ceases. After removal of the catalyst by filtration, the filtrate is concentrated. To the residue is added 5N hydrogen chloride-ethyl acetate solution (2 ml), and the resulting mixture is diluted with ethyl ether (50 ml) to deposit 3(S)-[1(S)-ethoxycarbonyl-5-(4-piperidyl)pentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid dihydrochloride (0.45 g) as a colorless precipitate. This acid is dissolved in 1N sodium hydroxide solution (15 ml), and the resulting solution is allowed to stand for 30 minutes at room temperature. After addition of acetic acid (3 ml), the mixture is subjected to MCI gel column chromatography using water-methanol (2:1) as an eluent. The eluate is concentrated in vacuo and lyophilized to yield 3(S)-[1(S)-carboxy-5-(4-piperidyl)pentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid (0.3 g) as colorless powder.

Workup

  1. custompressure until the absorption of hydrogen ceases
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. concentrationthe filtrate is concentrated
  5. additionTo the residue is added 5N hydrogen chloride-ethyl acetate solution (2 ml)
  6. additionthe resulting mixture is diluted with ethyl ether (50 ml)
  7. dissolutionThis acid is dissolved in 1N sodium hydroxide solution (15 ml)
  8. additionAfter addition of acetic acid (3 ml)
  9. concentrationThe eluate is concentrated in vacuo

Sources & evidence

ORD record
ord-db62bbbf694f465bb051be28a5425a5a
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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