HCID 22719737, compound → HCID 19775835, compound

HRID 1582071Notes

Reaction equation

HRID 1582071 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH:7]([CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[CH2:8][C:9]1([C:14]([NH:16][CH:17]2[CH2:22][CH2:21][CH:20]([C:23]([O:25]CC3C=CC=CC=3)=[O:24])[CH2:19][CH2:18]2)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].O.C(O)C>[C:1]([O:5][C:6](=[O:39])[CH:7]([CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[CH2:8][C:9]1([C:14]([NH:16][CH:17]2[CH2:18][CH2:19][CH:20]([C:23]([OH:25])=[O:24])[CH2:21][CH2:22]2)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 1

HCID 22719737HCID 22719737, compound

Product 1

HCID 19775835HCID 19775835, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of benzyl 4-{[(1-{3-tert-butoxy-2-[(2-methoxyethoxy)methyl]-3-oxopropyl}cyclopentyl)carbonyl]amino}cyclohexanecarboxylate (EP 274234), and 10% palladium on charcoal (250 mg) in water (10 ml) and ethanol (50 ml) was hydrogenated at 50 psi and room temperature for 18 hours. The reaction mixture was filtered through Solkafloc®, the filtrate concentrated under reduced pressure and the residue azeotroped with toluene (3×) and then dichloromethane (3×), to give the title compound, 2.0 g, 96%; 1H NMR (CDCl3, 300 MHz) δ: 1.48 (s, 9H), 1.53-1.84 (m, 14H), 1.94-2.10 (m, 5H), 2.60 (m, 2H), 3.40 (s, 3H), 3.41-3.63 (m, 5H), 3.96 (m, 1H), 5.90 (bd, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Solkafloc®
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customthe residue azeotroped with toluene (3×)

Sources & evidence

ORD record
ord-697167f7163c494fa4f2299992260432
Source dataset
uspto-grants-2004_05
Patent number
US06734186B1

Reaction notes

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