HCID 54464950, compound → HCID 53976939, compound

HRID 369453Notes

Reaction equation

HRID 369453 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16](=[O:31])[C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[CH:19][CH:18]=2)[C@H:10]([NH:32][C:33](=[O:50])[C:34]2[CH:39]=[CH:38][C:37]([O:40][C:41](=[O:49])[C:42]3[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=3)=[CH:36][CH:35]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16](=[O:31])[C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[C@H:10]([NH:32][C:33](=[O:50])[C:34]2[CH:39]=[CH:38][C:37]([O:40][C:41](=[O:49])[C:42]3[CH:43]=[CH:44][C:45]([F:48])=[CH:46][CH:47]=3)=[CH:36][CH:35]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 54464950HCID 54464950, compound

Product 1

HCID 53976939HCID 53976939, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

80 mg (3R,4R)-4-(4-Benzyloxy-benzoyloxy)-3-[4-(4-fluoro-benzoyloxy)-benzoylamino]-azepane-1-carboxylic acid tert-butyl ester was dissolved in tetrahydrofuran. 10 mg 5% palladium on charcoal was added and the mixture hydrogenated at atmospheric pressure and room temperature for 2 hours. The catalyst was filtered on, the pad washed with tetrahydrofuran and the filtrate evaporated under reduced pressure. The residue was purified by chromatography on silica gel (10 g, AcOEt/Hexane 1:1 eluent) to afford 56 mg (80% yield) (3R,4R)-3-[4-(4-Fluoro-benzoyloxy)-benzoylamino]-4-(4-hydroxy-benzoyloxy)-azepane-1-carboxylic acid tert-butyl ester as a colorless foam

Workup

  1. filtrationThe catalyst was filtered on, the pad
  2. washwashed with tetrahydrofuran
  3. customthe filtrate evaporated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (10 g, AcOEt/Hexane 1:1 eluent)

Sources & evidence

ORD record
ord-b38740c50fd44b54986befa82e8eebc8
Source dataset
uspto-grants-2000_10
Patent number
US06136969

Reaction notes

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