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(R)-1-[3-[[3-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester → (R)-1-[3-[[3-[(R)-2-Carboxy-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid

HRID 1583194
Notes
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Reaction equation

HRID 1583194 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:42])[CH2:17][CH2:18][N:19]([CH2:23][CH2:24][C:25]([N:27]1[CH2:31][CH2:30][CH2:29][C@@H:28]1[C:32]([O:34]CC1C=CC=CC=1)=[O:33])=[O:26])[CH2:20][CH2:21][CH3:22])=[O:10])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:32]([C@H:28]1[CH2:29][CH2:30][CH2:31][N:27]1[C:25](=[O:26])[CH2:24][CH2:23][N:19]([CH2:20][CH2:21][CH3:22])[CH2:18][CH2:17][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@@H:11]1[C:9]([OH:10])=[O:8])=[O:42])([OH:34])=[O:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 54362609(R)-1-[3-[[3-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 54332800(R)-1-[3-[[3-[(R)-2-Carboxy-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938Palladium
Catalyst
HCID 702EthanolSolvent

Procedure

A solution of 84 mg (0.15 mmol) (R)-1-[3-[[3-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester in 3 ml ethanol was stirred with 10 mg 10% palladium on charcoal under 1 atm of hydrogen for 16 h at room temperature. After filtration to remove the catalyst, concentration in vacuo afforded 58 mg (100%) of the title compound as a white solid. MS m/e (%): 398 (M+H+, 100).

Workup

  1. filtrationAfter filtration
  2. customto remove
  3. concentrationthe catalyst, concentration in vacuo

Sources & evidence

ORD record
ord-e453c9fc4a4842e4ae1c63a2af769cf8
Source dataset
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06740760B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes