Potassium Hydroxide → HCID 53996740, compound

HRID 1905642Notes

Reaction equation

HRID 1905642 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]([OH:32])[CH2:20][NH:21][C:22]([CH3:31])([CH2:24][CH2:25][N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)[CH3:23])=[CH:15][C:10]=1[NH:11]C(=O)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>O>[NH2:11][C:10]1[CH:15]=[C:16]([CH:19]([OH:32])[CH2:20][NH:21][C:22]([CH3:23])([CH2:24][CH2:25][N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)[CH3:31])[CH:17]=[CH:18][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54519175HCID 54519175, compound

Product 1

HCID 53996740HCID 53996740, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15 gm of 2'-benzyloxy-5'-[1-hydroxy-2-[4-(1-imidazolyl)-2-methyl-2-butylamino]-ethyl]-acetanilide (m.p. of the dioxalate 160°-163° C.), 18.5 gm of KOH, 80 ml of alcohol and 15 ml of water was refluxed for 24 hours, and the resulting 1-(3-amino-4-benzyloxy-phenyl)-2-[4-(1-imidazolyl)-2-methyl-2-butylamino]-ethanol was isolated as the trioxalate (m.p. 95°-100° C.). Aqueous ammonia was used to liberate the base which was reacted with potassium cyanate to form 1-{2'-benzyloxy-5'-[1-hydroxy-2-[4-(1-imidazolyl)-2-methyl-2-butylamino]-ethyl]-phenyl}-urea (m.p. 142°-143° C.). Catalytic hydrogenation of 5.1 gm of this compound in 100 ml of methanol with palladium charcoal as the catalyst yielded 3.5 gm of 1-{2'-hydroxy-5'-[1-hydroxy-2-]-4-(1-imidazolyl)-2-methyl-2-butylamino]-ethyl]-phenyl]-phenyl}-urea, whose sulfate of the formula ##STR76## had a melting point of 243°-244° C. The yield was 70% of theory.

Workup

  1. temperaturewas refluxed for 24 hours

Sources & evidence

ORD record
ord-2bb1acb097294540a22dcf221ea2fd99
Source dataset
uspto-grants-1987_03
Patent number
US04647563

Reaction notes

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