Methanol → HCID 70381997, compound

HRID 1762952Notes

Reaction equation

HRID 1762952 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[C:13]([C:16](=[O:36])[C:17](C(C)C)([NH2:32])C1C=CC(OCC3C=CC=CC=3)=CC=1)[CH:12]=[CH:11][C:10]=2[OH:37])=[O:6])[CH3:3].[CH3:38][OH:39]>[C].[Pd]>[ClH:1].[CH2:2]([O:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[C:13]([CH:16]([OH:36])[CH2:17][NH:32][CH:9]([CH3:10])[CH2:14][C:13]1[CH:16]=[CH:17][C:38]([OH:39])=[CH:11][CH:12]=1)[CH:12]=[CH:11][C:10]=2[OH:37])=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 70382448HCID 70382448, compound

Product 1

HCID 70381997HCID 70381997, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

209 mg of 4-[2-(4-benzyloxyphenyl)-1-methylethyl-aminoacetyl]-7-hydroxyindole-2-carboxylic acid ethyl ester hydrochloride is hydrogenated in 20 ml of methanol for 2.5 hours at room temperature and under normal pressure in the presence of 42 mg of 10% palladium-carbon. The mixture is filtered, the filtrate is concentrated under vacuum, and the residue is recrystallized from acetone/diethyl ether, thus obtaining 115 mg of 4-{1-hydroxy-2-[2-(4-hydroxyphenyl)-1-methylethylamino]ethyl}-7-hydroxy-indole-2-carboxylic acid ethyl ester hydrochloride, decomposition point 110° C.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated under vacuum
  3. customthe residue is recrystallized from acetone/diethyl ether

Sources & evidence

ORD record
ord-5de18ea45ddb4fa799f6dd6db5e372f2
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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