HCID 67499497, compound → HCID 9906098, compound

HRID 1919347Notes

Reaction equation

HRID 1919347 reaction equation
[C:1]([O:5][CH:6]([O:10][C:11]([NH:13][CH2:14][C:15]1([CH2:21][C:22]([O:24]CC2C=CC=CC=2)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:12])[CH2:7][CH2:8][CH3:9])(=[O:4])[CH2:2][CH3:3]>C(O)C.[Pd]>[C:1]([O:5][CH:6]([O:10][C:11]([NH:13][CH2:14][C:15]1([CH2:21][C:22]([OH:24])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:12])[CH2:7][CH2:8][CH3:9])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 67499497HCID 67499497, compound

Product 1

HCID 9906098HCID 9906098, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of (135) (2.5 g, 5.77 mmol) and 10% Pd/C (250 mg) in ethanol (100 mL) was stirred under an atmosphere of hydrogen (balloon) for 30 minutes then was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to afford the crude product, which was purified by preparative LC-MS to give 1.21 g of the desired acid (131). (CDCl3, 400 MHz): 0.97 (t, J=7.2 Hz, 3H), 1.15 (t, J=7.2 Hz, 3H), 1.50-1.38 (m, 12H), 1.72 (m, 21-1), 2.32 (m, 4H), 3.18 (dd, J=6.4, 4.4 Hz, 2H), 5.27 (t, J=6.4 Hz, 1H), 6.72 (t, J=5.6 Hz, 1H). MS (ESI) m/z 344.39 (M+H)+.

Workup

  1. filtrationthen was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto afford the crude product, which
  4. customwas purified by preparative LC-MS

Sources & evidence

ORD record
ord-3a231295732748aa89d69499d3446dbd
Source dataset
uspto-grants-2012_05
Patent number
US08168623B2

Reaction notes

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