tert-butyl 3-({1-[2-(benzyloxy)-2-oxoethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl}methyl)-1H-indazole-1-carboxylate → (3-{[1-(tert-butoxycarbonyl)-1H-indazol-3-yl]methyl}-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetic acid

HRID 1375367Notes

Reaction equation

HRID 1375367 reaction equation
C([O:8][C:9](=[O:47])[CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14](=[O:28])[CH:13]([CH2:29][C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[N:31]=2)[C:12]1=[O:46])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:42]([O:41][C:39]([N:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30]([CH2:29][CH:13]2[C:12](=[O:46])[N:11]([CH2:10][C:9]([OH:47])=[O:8])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:14]2=[O:28])=[N:31]1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

4

Reactant 1

HCID 69426247tert-butyl 3-({1-[2-(benzyloxy)-2-oxoethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl}methyl)-1H-indazole-1-carboxylate

Product 1

HCID 69423828(3-{[1-(tert-butoxycarbonyl)-1H-indazol-3-yl]methyl}-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetic acidYield 85.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(0.3 g, 0.95 mM) of tert-butyl 3-({1-[2-(benzyloxy)-2-oxoethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl}methyl)-1H-indazole-1-carboxylate were dissolved in 10 ml of ethyl acetate and 50 mg of 10% Pd/C were added. Reaction mixture was hydrogenated at atm. Pressure overnight. Catalyst was removed by filtration and was solvent evaporated under reduced pressure. 0.22 g of product was obtained.

Workup

  1. customReaction mixture
  2. customPressure overnight
  3. customCatalyst was removed by filtration
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-270f55e9f13f46a4b95459fdd24cbd6b
Source dataset
uspto-grants-2007_01
Patent number
US07169773B2

Reaction notes

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