Sodium Sulfite → (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetic acid

HRID 510261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510261
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:19][OH:20])[C:8]([CH3:26])=[CH:7][C:5]=2[N:6]=1.[O-:27]S([O-])=O.[Na+].[Na+]>C(#N)C.O.CCOC(C)=O>[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)=[C:9]([C@H:18]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[C:19]([OH:27])=[O:20])[C:8]([CH3:26])=[CH:7][C:5]=2[N:6]=1

Komponenten

6

Edukt 2

HCID 24437Sodium SulfiteHCID 86699791(S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol

Produkt 1

HCID 86699792(S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol (1.95 g, 5.00 mmol) in acetonitrile (25 mL) and water (1 mL) was added H5IO6 (1.37 g, 6.00 mmol) and CrO3 (1.00 g, 10.0 mmol). The mixture was stirred at rt for 1 h and was diluted with EtOAc (50 mL) and a saturated solution of Na2SO3 (50 mL). The layers were separated, and the aqueous layer was extracted with EtOAc. The crude material was taken on without further purification. 1H-NMR: 400 MHz, (CDCl3) δ: 7.42-7.61 (m, 4H), 7.20 (s, 1H), 5.11 (s, 1H), 2.47 (s, 3H), 0.93 (s, 9H).

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. customThe crude material was taken on without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d5a73a013cf14a6590c636489dae1ede
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096586B2

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