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

HRID 1583196Notes

Reaction equation

HRID 1583196 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:43])[CH2:17][CH2:18][N:19]([CH2:24][CH2:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@@H:29]1[C:33]([O:35]CC1C=CC=CC=1)=[O:34])=[O:27])[CH2:20][CH:21]1[CH2:23][CH2:22]1)=[O:10])C1C=CC=CC=1.[H][H]>C(O)(C)C.[Pd]>[C:33]([C@H:29]1[CH2:30][CH2:31][CH2:32][N:28]1[C:26](=[O:27])[CH2:25][CH2:24][N:19]([CH2:20][CH:21]1[CH2:22][CH2:23]1)[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:43])([OH:35])=[O:34]

Participants

5

Reactant 2

HCID 54033103(R)-1-[3-[[3-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-cyclopropylmethyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 53973450(R)-1-[3-[[3-[(R)-2-Carboxy-pyrrolidin-1-yl]-3-oxo-propyl]-cyclopropylmethyl-amino]-propionyl]-pyrrolidine-2-carboxylic acidYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 220 mg (0.37 mmol) (R)-1-[3-[[3-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-cyclopropylmethyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester in 20 ml isopropanol 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 153 mg (100%) of the title compound as a yellow solid. MS m/e (%): 408 ([M−H]−, 100).

Workup

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

Sources & evidence

ORD record
ord-f508bf875326478982a62f243de06919
Source dataset
uspto-grants-2004_05
Patent number
US06740760B2

Reaction notes

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