Ethyl Acetate → HCID 86588612, compound

HRID 1759787Notes

Reaction equation

HRID 1759787 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:26]1[CH:35]=[CH:34][C:33]2[C:32]([CH3:37])([CH3:36])[CH2:31][CH2:30][C:29]([CH3:39])([CH3:38])[C:28]=2[CH:27]=1)[C:14](=[O:25])[NH:15][C:16]1[CH:24]=C[C:19](C(O)=O)=[CH:18][CH:17]=1)C1C=CC=CC=1.[H][H].[C:42]([O:45]CC)(=[O:44])[CH3:43]>[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:26]1[CH:35]=[CH:34][C:33]2[C:32]([CH3:37])([CH3:36])[CH2:31][CH2:30][C:29]([CH3:39])([CH3:38])[C:28]=2[CH:27]=1)[C:14](=[O:25])[NH:15][C:16]1[CH:24]=[C:43]([CH:19]=[CH:18][CH:17]=1)[C:42]([OH:45])=[O:44]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10165315HCID 10165315, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86588612HCID 86588612, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 4-[3-(4-benzyloxy-butyl)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (41) (0.51 g, 0.96 mmole) in 50 mL ethyl acetate, containing 80 mg of 10% palladium on charcoal, was maintained under 1 atmosphere of hydrogen overnight. The mixture was filtered over Celite and volatile material was removed in vacuo. Trituration in hexanes afforded 380 mg (90%) of 4-[3-(4-hydroxy-butyl)-3-(5,5,8,8-tetramethyl -5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (71) as a white solid. M.P. 124-125° C.

Workup

  1. filtrationThe mixture was filtered over Celite and volatile material
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-54f1e5d3780a44ae861d09be4cc74d08
Source dataset
uspto-grants-2005_01
Patent number
US06838472B2

Reaction notes

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