Toluene → (R)-4-Hydroxy-7-(1-hydroxy-2-(4-(2-(4-(5-methylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzylamino)ethyl)benzo[d]thiazol-2(3H)-one formate

HRID 471247ノート

反応式

HRID 471247 の反応式
FC(F)(F)[C:3]([OH:5])=[O:4].[OH:8][C@H:9]([C:48]1[C:56]2[S:55][C:54](=[O:57])[NH:53][C:52]=2[C:51]([OH:58])=[CH:50][CH:49]=1)[CH2:10][N:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]2[CH2:47][CH2:46][C:32]3([O:37][CH2:36][CH2:35][N:34]([C:38]([C:40]4[CH:44]=[C:43]([CH3:45])[S:42][CH:41]=4)=[O:39])[CH2:33]3)[CH2:31][CH2:30]2)=[CH:22][CH:21]=1)C(=O)OC(C)(C)C.C1(C)C=CC=CC=1>C(Cl)Cl>[CH:3]([OH:5])=[O:4].[OH:58][C:51]1[C:52]2[NH:53][C:54](=[O:57])[S:55][C:56]=2[C:48]([C@@H:9]([OH:8])[CH2:10][NH:11][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:47][CH2:46][C:32]4([O:37][CH2:36][CH2:35][N:34]([C:38]([C:40]5[CH:44]=[C:43]([CH3:45])[S:42][CH:41]=5)=[O:39])[CH2:33]4)[CH2:31][CH2:30]3)=[CH:22][CH:21]=2)=[CH:49][CH:50]=1

参加物

5

反応物 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989077(R)-tert-Butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(4-(2-(4-(5-methylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl)carbamate

生成物 1

HCID 67291950(R)-4-Hydroxy-7-(1-hydroxy-2-(4-(2-(4-(5-methylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzylamino)ethyl)benzo[d]thiazol-2(3H)-one formate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (1.2 mL) was added to a solution of (R)-tert-butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(4-(2-(4-(5-methylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl)carbamate (example 104, step c) (0.33 g) in DCM (5 mL) and the resulting mixture stirred for 10 minutes. Toluene (20 mL) was added and the mixture was evaporated in vacuo. The residue was azeotroped with toluene (3×20 mL). Purification was by preparative HPLC (Phenomenex Gemini®, Gradient: 5-40% acetonitrile in 0.1% aqueous formic acid). The fractions containing product were combined and freeze-dried to give the titled compound as a white solid. Yield 0.12 g.

後処理

  1. customthe mixture was evaporated in vacuo
  2. customThe residue was azeotroped with toluene (3×20 mL)
  3. customPurification
  4. additionThe fractions containing product
  5. customfreeze-dried

出典と根拠

ORDレコード
ord-61290f5f7f284079b30e3adac2eaaed1
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

読み込み中…