1-[N-[2-(4-carbamoyl-3-hydroxy-phenoxy)-1-methyl-ethyl]-benzylamino]-3-(4-methane-sulfonylamino-phenoxy)-2-propanol → HCID 13754397, compound

HRID 4551Notes

Reaction equation

HRID 4551 reaction equation
[C:1]([C:4]1[CH:37]=[CH:36][C:7]([O:8][CH2:9][CH:10]([N:12](CC2C=CC=CC=2)[CH2:13][CH:14]([OH:28])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=2)[CH3:11])=[CH:6][C:5]=1[OH:38])(=[O:3])[NH2:2]>CO.[Pd]>[C:1]([C:4]1[CH:37]=[CH:36][C:7]([O:8][CH2:9][CH:10]([NH:12][CH2:13][CH:14]([OH:28])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])=[CH:19][CH:18]=2)[CH3:11])=[CH:6][C:5]=1[OH:38])(=[O:3])[NH2:2]

Participants

4

Reactant 1

HCID 201513761-[N-[2-(4-carbamoyl-3-hydroxy-phenoxy)-1-methyl-ethyl]-benzylamino]-3-(4-methane-sulfonylamino-phenoxy)-2-propanol

Product 1

HCID 13754397HCID 13754397, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 20.0 g of crude 1-[N-[2-(4-carbamoyl-3-hydroxy-phenoxy)-1-methyl-ethyl]-benzylamino]-3-(4-methanesulfonylamino-phenoxy)-2-propanol in 250 ml of methanol is hydrogenated, after the addition of 2.5 g of Pd/C catalyst (5%), under normal conditions until debenzylation is completed (DC control), for which an addition of a further 1.0 g of catalyst is required. The catalyst is filtered off; the filtrate is concentrated by evaporation, and the oil remaining behind is dissolved in a small amount of hot isopropanol. On cooling is obtained crystalline 1-[2-(4-carbamoyl-3-hydroxy-phenoxy)-1-methyl-ethylamino]-3-(4-methanesulfonylamino-phenoxy)-2-propanol, m.p. 147°-150° (diastereoisomeric mixture).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated by evaporation
  3. dissolutionthe oil remaining behind is dissolved in a small amount of hot isopropanol
  4. temperatureOn cooling

Sources & evidence

ORD record
ord-13fff069e6674f938ae4987e19fdf4d8
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Reaction notes

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