HCID 131726929, compound → HCID 131726928, compound

HRID 132704Notes

Reaction equation

HRID 132704 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:58][CH:59]([CH3:61])[CH3:60])[C@@H:12]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:57])[CH:38]([NH:52][C:53]([O:55][CH3:56])=[O:54])[CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:13][O:14][C:15](=[O:31])[C@@H:16]([NH:20]C(OCC2C=CC=CC=2)=O)[CH:17]([CH3:19])[CH3:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1>C1COCC1.[Pd]>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:58][CH:59]([CH3:61])[CH3:60])[C@@H:12]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:57])[CH:38]([NH:52][C:53]([O:55][CH3:56])=[O:54])[CH:39]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:13][O:14][C:15](=[O:31])[C@@H:16]([NH2:20])[CH:17]([CH3:18])[CH3:19])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 131726929HCID 131726929, compound

Product 1

HCID 131726928HCID 131726928, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (2S,2S)-2-benzyloxycarbonylamino-3-methyl-butyric acid 2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-(2-methoxy carbonylamino-3,3-diphenyl-propionylamino)-hexyl ester (step C, 120 mg, 0.14 mmol) in anhydrous THF (8 mL), under nitrogen atmosphere, was added palladium 10% wt. on activated carbon (160 mg). The mixture was reacted under hydrogen atmosphere overnight, at room temperature. The solution was filtered and the palladium on carbon was washed with THF (50 mL). The solvent was evaporated and the residue (110 mg) was purified by flash chromatography using ethyl acetate as the eluent. The clear oil was obtained in 47% yield (47 mg).

Workup

  1. customThe mixture was reacted under hydrogen atmosphere overnight, at room temperature
  2. filtrationThe solution was filtered
  3. washthe palladium on carbon was washed with THF (50 mL)
  4. customThe solvent was evaporated
  5. customthe residue (110 mg) was purified by flash chromatography
  6. customThe clear oil was obtained in 47% yield (47 mg)

Sources & evidence

ORD record
ord-297f092adfb142fab892a642b70dcf1d
Source dataset
uspto-grants-2008_06
Patent number
US07388008B2

Reaction notes

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