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 471247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471247
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

Komponenten

5

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-61290f5f7f284079b30e3adac2eaaed1
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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