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Toluene → (R)-7-(2-(4-(2-(4-(Benzo[d]thiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzylamino)-1-hydroxyethyl)-4-hydroxybenzo[d]thiazol-2(3H)-one formate

HRID 471252
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HRID 471252 반응식
FC(F)(F)[C:3]([OH:5])=[O:4].[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]([N:19]1[CH2:24][C:23]2([CH2:29][CH2:28][N:27]([CH2:30][CH2:31][O:32][C:33]3[CH:61]=[CH:60][C:36]([CH2:37][N:38]([CH2:46][C@H:47]([OH:59])[C:48]4[C:56]5[S:55][C:54](=[O:57])[NH:53][C:52]=5[C:51]([OH:58])=[CH:50][CH:49]=4)C(=O)OC(C)(C)C)=[CH:35][CH:34]=3)[CH2:26][CH2:25]2)[O:22][CH2:21][CH2:20]1)=[O:18].C1(C)C=CC=CC=1>C(Cl)Cl>[CH:3]([OH:5])=[O:4].[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]([N:19]1[CH2:24][C:23]2([CH2:29][CH2:28][N:27]([CH2:30][CH2:31][O:32][C:33]3[CH:61]=[CH:60][C:36]([CH2:37][NH:38][CH2:46][C@@H:47]([C:48]4[C:56]5[S:55][C:54](=[O:57])[NH:53][C:52]=5[C:51]([OH:58])=[CH:50][CH:49]=4)[OH:59])=[CH:35][CH:34]=3)[CH2:26][CH2:25]2)[O:22][CH2:21][CH2:20]1)=[O:18]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989166(R)-tert-Butyl 4-(2-(4-(benzo[d]thiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)carbamate

생성물 1

HCID 67292606(R)-7-(2-(4-(2-(4-(Benzo[d]thiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzylamino)-1-hydroxyethyl)-4-hydroxybenzo[d]thiazol-2(3H)-one formate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (1.25 mL) was added to a solution of (R)-tert-butyl 4-(2-(4-(benzo[d]thiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)carbamate (example 106, step c) (0.33 g) in DCM (4 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 0.096 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-185816e038e24496a298ebc6e94672a6
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08629271B2

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