Ammonia → 1-(4-Carbamoyl-3-hydroxyphenoxy)-3-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]propan-2-ol

HRID 4543Notes

Reaction equation

HRID 4543 reaction equation
[NH3:1].[C:2]([C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][C:31]=1[OH:32])[O:8][CH2:9][CH:10]([NH:12][CH2:13][CH:14]([OH:28])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](OC)=[O:24])=[C:19]([OH:27])[CH:18]=1)[CH3:11])(=[O:4])[NH2:3]>O1CCOCC1>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH:14]([OH:28])[CH2:13][NH:12][CH:10]([CH3:11])[CH2:9][O:8][C:7]2[CH:29]=[CH:30][C:31]([OH:32])=[C:5]([C:2](=[O:4])[NH2:3])[CH:6]=2)=[CH:18][C:19]=1[OH:27])(=[O:24])[NH2:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13754384HCID 13754384, compound

Product 1

HCID 137543831-(4-Carbamoyl-3-hydroxyphenoxy)-3-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]propan-2-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 50 ml of dioxan and 500 ml of concentrated ammonia solution is added to 21.5 g of 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]-3-(3-hydroxy-4-methoxycarbonylphenoxy)propan-2-ol. The reaction mixture is stirred for 1-2 hours, and as soon as it is homogeneous, left to stand for 3 days at 20°-30°. By concentration by evaporation, 20 g of crude, crystalline 1-(4-carbamoyl-3-hydroxyphenoxy)-3-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]propan-2-ol is obtained as a diastereoisomeric mixture having a melting point of 180°-190°. A hydrochloride is formed which melts at 238°-243° (from ethanol/methanol).

Workup

  1. waitleft
  2. waitto stand for 3 days at 20°-30°
  3. concentrationBy concentration
  4. customby evaporation, 20 g of crude

Sources & evidence

ORD record
ord-b1956ecd3bfc4500ac0ede3e046b88ed
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Reaction notes

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