1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol → 1-[2-(3-Carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol

HRID 638058Notes

Reaction equation

HRID 638058 reaction equation
C([N:8]([CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([C:35](=[O:37])[NH2:36])[CH:29]=1)[CH2:9][CH:10]([OH:24])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[CH:15][CH:14]=1)C1C=CC=CC=1>[Pd].C(O)(=O)C.FC(F)(F)C(O)=O>[C:35]([C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[OH:34])[O:27][CH2:26][CH2:25][NH:8][CH2:9][CH:10]([OH:24])[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[CH:17][CH:18]=1)(=[O:37])[NH2:36]

Participants

5

Reactant 1

HCID 202550681-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol

Product 1

HCID 202551621-[2-(3-Carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

After the addition of 0.69 g of palladium-on-carbon catalyst (10%), a solution of 3.0 g of crude 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol in a mixture of 30 ml of glacial acetic acid and 3 ml of trifluoroacetic acid is hydrogenated at 45° and normal pressure until the absorption of hydrogen has ceased. The suspension is filtered through a filter aid and the filtrate is freed of solvent; ice water is added to the residue, the pH is adjusted to approximately 9 with ammonia and extraction is carried out several times with ethyl acetate. The combined organic phases are dried over sodium sulphate, concentrated by evaporation and the residue is recrystallised from isopropanol, yielding 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol having a melting point of 136°-138°.

Workup

  1. customis hydrogenated at 45°
  2. customnormal pressure until the absorption of hydrogen
  3. filtrationThe suspension is filtered through a filter aid
  4. additionice water is added to the residue
  5. extractionthe pH is adjusted to approximately 9 with ammonia and extraction
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated by evaporation
  8. customthe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-74f4e2b6216f4c37afd52f83bfe4ad42
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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