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 638058ノート

反応式

HRID 638058 の反応式
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]

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-74f4e2b6216f4c37afd52f83bfe4ad42
出典データセット
uspto-grants-1985_12
特許番号
US04559354

反応ノート

読み込み中…