Ammonium formate → (S)-4-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)-5-tert-butoxy-5-oxopentanoic acid

HRID 56322Notes

Reaction equation

HRID 56322 reaction equation
O=C([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[NH:17][C:18](=[O:40])[NH:19][C@H:20]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:21][CH2:22][C:23]([O:25]CC1C=CC=CC=1)=[O:24])OCC1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:17][C:18](=[O:40])[NH:19][C@H:20]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59404356(9S,13S)-15-benzyl 13,9-di-tert-butyl 3,11-dioxo-1-phenyl-2-oxa-4,10,12-triazapentadecane-9,13,15-tricarboxylate

Product 1

HCID 59404303(S)-4-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)-5-tert-butoxy-5-oxopentanoic acidYield 142%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of (9S,13S)-15-benzyl 13,9-di-tert-butyl 3,11-dioxo-1-phenyl-2-oxa-4,10,12-triazapentadecane-9,13,15-tricarboxylate (4.30 g, 6.64 mmol), 10% Pd/C (1.0 g) and ammonium formate (4.0 g) in EtOH (70 mL) under a empty balloon was stirred at room temperature overnight. The reaction mixture was filtered through a pad of celite and washed with EtOAc. The solvent was evaporated to give (S)-4-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)-5-tert-butoxy-5-oxopentanoic acid (4.07 g, 70%) which was used without further purification. ESMS m/z: 432.3 (M/2+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashed with EtOAc
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ae0ca77785434f9faa1357c408d80f3b
Source dataset
uspto-grants-2016_09
Patent number
US09433594B2

Reaction notes

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