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 1689477노트

반응식

HRID 1689477 반응식
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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c95fa695063d4335b96008d425a65f82
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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