HCID 67304771, compound → HCID 58444238, compound

HRID 1009833Notes

Reaction equation

HRID 1009833 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][C@@H:14]([C:16](=[O:18])[CH3:17])[C@H:13]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:20]=2)[N:12]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:10])C1C=CC=CC=1>CO.[Pd]>[C:36]([O:35][C:33]([N:12]1[C@@H:13]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:20]=2)[C@H:14]([C:16](=[O:18])[CH3:17])[CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:34])([CH3:37])([CH3:38])[CH3:39]

Participants

4

Reactant 1

HCID 67304771HCID 67304771, compound

Product 1

HCID 58444238HCID 58444238, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The other isomer at position 4 may be prepared as follows: A solution of (2S,4R,5R)-4-Acetyl-5-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester benzyl ester (0.58 g) in 8 mL of methanol is treated with 0.058 g of 10% Pd/C and placed under an atmosphere of hydrogen for 90 minutes at room temperature. The catalyst is removed by filtration and the solvent removed completely to give 0.44 g of the desired compound as a viscous oil. 1H-NMR δ (d6-DMSO): 12.90 (1H, Brs, exch D2O, CO2H), 7.40 (1H, m, Ph), 6.95 (1H, m, Ph), 6.80 (1H, m. Ph), 5.17 (1H, d, PhCHN), 4.13 (1H, m NCHCO2), 4.01 (2H, m, CH2O), 3.73 (3H, s, CH3O), 3.55-3.45 (3H, m, CHCO+CH2O), 3.25 (3H, s, CH3O), 2.40-2.15 (2H, s, CH2-ring), 1.93 (2H, m, CH2), 1.85 (3H, s, Me), 1.28 (9H, s, tBu).

Workup

  1. customThe other isomer at position 4 may be prepared
  2. customThe catalyst is removed by filtration
  3. customthe solvent removed completely

Sources & evidence

ORD record
ord-b1a1f5a3f2e747849c851de067506d79
Source dataset
uspto-grants-2011_07
Patent number
US07973175B2

Reaction notes

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