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

HRID 1689487
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HRID 1689487 반응식
FC(F)(F)[C:3]([OH:5])=[O:4].[OH:8][C@H:9]([C:50]1[C:58]2[S:57][C:56](=[O:59])[NH:55][C:54]=2[C:53]([OH:60])=[CH:52][CH:51]=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[CH2:49][CH2:48][C:32]3([O:37][CH2:36][CH2:35][N:34]([C:38]([C:40]4[N:41]=[C:42]([CH:45]([CH3:47])[CH3:46])[S:43][CH:44]=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:60][C:53]1[C:54]2[NH:55][C:56](=[O:59])[S:57][C:58]=2[C:50]([C@@H:9]([OH:8])[CH2:10][NH:11][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][C:32]4([O:37][CH2:36][CH2:35][N:34]([C:38]([C:40]5[N:41]=[C:42]([CH:45]([CH3:47])[CH3:46])[S:43][CH:44]=5)=[O:39])[CH2:33]4)[CH2:48][CH2:49]3)=[CH:24][CH:25]=2)=[CH:51][CH:52]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989138(R)-tert-Butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl)carbamate

생성물 1

HCID 67292711(R)-4-Hydroxy-7-(1-hydroxy-2-(4-(2-(4-(2-isopropylthiazole-4-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 (0.7 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-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl)carbamate (example 108, step d) (0.122 g) in DCM (1.5 mL). The resulting mixture was stirred at RT for 10 min. Toluene (15 mL) was added and the reaction mixture was evaporated in vacuo. The residue was azeotroped twice with MeCN. The viscous yellow residue was purified by 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 0.052 g.

후처리

  1. customthe reaction mixture was evaporated in vacuo
  2. customThe residue was azeotroped twice with MeCN
  3. customThe viscous yellow residue was purified by HPLC (Phenomenex Gemini®, Gradient: 5-40% acetonitrile in 0.1% aqueous formic acid)
  4. additionThe fractions containing product
  5. customfreeze dried

출처 및 근거

ORD 기록
ord-9156930d01b1453fbd7077e2b3534e07
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08148373B2

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