HCID 59547335, compound → HCID 59547341, compound

HRID 2038555Notes

Reaction equation

HRID 2038555 reaction equation
C(OC([NH:11][C@@H:12]([C:38]([CH3:41])([CH3:40])[CH3:39])[C:13]([N:15]1[C@H:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][C@:17]2([O:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18]2)[CH2:16]1)=[O:14])=O)C1C=CC=CC=1>[Pd].CO>[NH2:11][C@@H:12]([C:38]([CH3:41])([CH3:40])[CH3:39])[C:13]([N:15]1[C@H:30]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:29][C@:17]2([O:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18]2)[CH2:16]1)=[O:14]

Participants

4

Reactant 1

HCID 59547335HCID 59547335, compound

Product 1

HCID 59547341HCID 59547341, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium (10%) on carbon (100 mg) was wetted with MeOH (2.5 mL) and added to (5S,8S)-tert-butyl 7-((S)-2-(benzyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-3-phenyl-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (E1) (323 mg, 411 mot, 1 eq.). The reaction was hydrogenated at 50 psi overnight at room temp., then filtered and concentrated to give (5S,8S)-tert-butyl 7-((S)-2-amino-3,3-dimethylbutanoyl)-2-oxo-3-phenyl-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (F1) in quantitative yield. LC MS+: 432.39 at 1.94 min (10-90%, 3-5 min, Formic Acid).

Workup

  1. customwas hydrogenated at 50 psi overnight at room temp.
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a2eb16fb08eb4db9a9002106efae6806
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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