HCID 54464950, compound → HCID 53976939, compound

HRID 1075695Notes

Reaction equation

HRID 1075695 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

80mg (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 1:1eluent) 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 1:1eluent)

Sources & evidence

ORD record
ord-f84ae02ce5944286a3e1f08975367528
Source dataset
uspto-grants-1999_05
Patent number
US05907038

Reaction notes

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