Hydrochloric Acid → HCID 69415564, compound

HRID 852887Notes

Reaction equation

HRID 852887 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][CH:6]([NH:22][C:23](=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14]CC2C=CC=CC=2)=[CH:10][CH:9]=1.Cl>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][CH:6]([NH:22][C:23](=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69414655HCID 69414655, compound

Product 1

HCID 69415564HCID 69415564, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(RS)-5-(4-Benzyloxy-phenyl)-4-(7-phenyl-heptanoylamino)-pentanoic acid methyl ester 78 (872 mg, 1.74 mmol) was hydrogenated over 10% Pd—C in THF (20 mL) containing HCl solution (1 M, 2.5 mL). The solution was filtered (Celite™) and approximately two thirds of the solvent removed under reduced pressure. The solution was diluted with water and extracted into EtOAc. The combined extracts were washed with water, brine and dried with MgSO4. Evaporation of the solvent in vacuo afforded the title compound (702 mg, 98%). ESMS 412 (M+H)+.

Workup

  1. filtrationThe solution was filtered (Celite™) and approximately two thirds of the solvent
  2. customremoved under reduced pressure
  3. additionThe solution was diluted with water
  4. extractionextracted into EtOAc
  5. washThe combined extracts were washed with water, brine
  6. dry with materialdried with MgSO4
  7. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-98e7e675071a4d938d1fdfcc6c791919
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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