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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 471257
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Reaktionsgleichung

Reaktionsgleichung von HRID 471257
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
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Komponenten

5

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d9946ed8e332480c95d9a0d964ae6612
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08629271B2

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