HCID 23520173, compound → HCID 59908504, compound

HRID 1008276Notes

Reaction equation

HRID 1008276 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C@@H:5]([CH2:23][CH2:24][CH2:25][CH3:26])[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([O:15]CC1C=CC=CC=1)=[O:14])=[O:7]>C(OC(=O)C)C.[Pd]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C@@H:5]([CH2:23][CH2:24][CH2:25][CH3:26])[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=[O:14])=[O:7]

Participants

4

Reactant 1

HCID 23520173HCID 23520173, compound

Product 1

HCID 59908504HCID 59908504, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of mono-4-methyl 2-(R)-butylsuccinic acid, (prepared in three steps from hexanoylchloride and t-butyl bromoacetate as described below; 1 mmol) in DMF was added proline O-benzyl ester (1 mmol), DIEA (0.4 mL, 2.3 mmol), and a coupling reagent (e.g. EDCI, PyBOP, DIC, etc.; 1 mmol). The mixture was stirred overnight, then diluted with ethyl acetate and washed with aqueous HCl (1 N), water, saturated sodium bicarbonate, brine, and then dried (Na2SO4). The filtrate was concentrated and then purified on silica gel (Merck 60; ethyl acetate/hexane) to afford methyl-3-(R)-butyl-3-(2-(S)-benzyloxycarbonylpyrrolidin-1-ylcarbonyl)propionate. To this amide (0.1 mmol) in ethylacetate (10 mL) was added 10% Pd/C (100 mg) and the solution stirred under a hydrogen atmosphere for 8 h. The suspension was filtered through a Celite plug and then concentrated to afford methyl-3-(R)-butyl-3-(2-(S)-carboxypyrrolidin-1-ylcarbonyl)propionate E-2.

Workup

  1. filtrationThe suspension was filtered through a Celite plug
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a13fc6940cec420da57b095d3fb044fa
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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