Hydrochloric Acid → HCID 178459249, compound

HRID 964707Notes

Reaction equation

HRID 964707 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:34][C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)[C@H:13]([C@H:24]2[CH2:29][CH2:28][C@H:27]([O:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:25]2)[C:14]([O:16]CC2C=CC=CC=2)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[ClH:41]>C(O)C.[Pd]>[ClH:41].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:34][C:35]2[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=2)[C@H:13]([C@H:24]2[CH2:29][CH2:28][C@H:27]([O:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:25]2)[C:14]([OH:16])=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178459248HCID 178459248, compound

Product 1

HCID 178459249HCID 178459249, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl 2(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-(trans-4-propoxycyclohexyl)-acetate (3.0 g, 5 mmol) in ethanol (50 mL) containing 3 N hydrochloric acid (5 mL, 15 mmol) is hydrogenated at 50 psi in the presence of 5% palladium on charcoal (200 mg) at room temperature for 4 hours. The reaction mixture is filtered through celite washing with ethanol and concentrated in vacuo to provide 2(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-(trans-4-propoxycyclohexyl) acetic acid hydrochloride as a crude product.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthrough celite washing with ethanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eef2654cab4f4f4fb8265273a915dc87
Source dataset
uspto-grants-1998_06
Patent number
US05770624

Reaction notes

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