Sodium Hydroxide → HCID 86700405, Verbindung

HRID 879591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879591
[C:1]([O:5][C@@H:6]([C:12]1[C:34]([CH3:35])=[CH:33][C:15]2[N:16]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][C:21]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)([CH3:25])[CH2:20]3)[S:18][C:14]=2[C:13]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([O:5][C@@H:6]([C:12]1[C:34]([CH3:35])=[CH:33][C:15]2[N:16]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][C:21]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)([CH3:25])[CH2:20]3)[S:18][C:14]=2[C:13]=1[C:36]1[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86700404HCID 86700404, Verbindung

Produkt 1

HCID 86700405HCID 86700405, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of (2S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(4-chlorophenyl)-2-methylmorpholino)-5-methylbenzo[d]thiazol-6-yl)acetate (63.7 mg, 0.101 mmol) in CH3OH/THF (1:1, 4 mL) was added NaOH (2N, 1 mL, 2 mmol), the resulting mixture was heated at 50° C. for 14 hr. The mixture was evaporated to a small volume, acidified to pH 3 and taken into partitioned between CH2Cl2 and brine. The organic layer was separated, dried (Na2SO4), filtered and evaporated to dryness. The residue was purified on CombiFlash (50% EtOAc/Hex) to give (2S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(4-chlorophenyl)-2-methylmorpholino)-5-methylbenzo[d]thiazol-6-yl)acetic acid. LCMS-ESI+: calc'd for C31H32Cl2N2O4S: 599.2, 601.2 (M+H+); found: 599.2, 601.2 (M+H+). 1H-NMR: 400 MHz, (CD3OD) δ: 7.62 (m, 1H), 7.44-7.53 (m, 5H), 7.32 (m, 3H), 5.13 (s, 1H), 4.31 (t, J=14.4 Hz, 1H), 3.81 (m, 1H), 3.62 (m, 1H), 3.44-3.53 (m, 3H), 2.50 (s, 3H), 1.46 (s, 3H), 0.95 (s, 9H).

Aufarbeitung

  1. customThe mixture was evaporated to a small volume
  2. custominto partitioned between CH2Cl2 and brine
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified on CombiFlash (50% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-a451ca9b3ac14fea8b30754425a9a031
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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