HCID 11101284, Verbindung → 3-t-Butoxycarbonylamino-3-methyl-N-[3,4-dihydro-1,4-dioxo-1,5-benzothiazepin-3(S)-yl]-butanamide

HRID 1591450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1591450
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@H:14]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[S:16][CH2:15]1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:29].[Na+]>CO.O>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@H:14]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[S:16](=[O:29])[CH2:15]1)=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 11101284HCID 11101284, VerbindungHCID 23667635Sodium periodate

Produkt 1

HCID 186514853-t-Butoxycarbonylamino-3-methyl-N-[3,4-dihydro-1,4-dioxo-1,5-benzothiazepin-3(S)-yl]-butanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of 179 mg (0.46 mmol) of 3-t-butoxycarbonylamino-3-methyl-N-[3,4-dihydro-4-oxo-1,5-benzothiazepin-3(S)-yl]-butanamide (Example 46, Step A) in 4.5 mL of methanol/water (5:1) was treated with 102 mg (0.48 mmol, 1.05 eq) of sodium periodate and stirred at room temperature for 48 hours. The reaction mixture was filtered and the filtrate concentrated under vacuum. The residue was redissolved in chloroform, dried over potassium carbonate, filtered and concentrated under vacuum. Purification by flash chromatography on silica, eluting with ethyl acetate, afforded 47 mg (0.12 mmol, 25%) of the less polar, minor diastereomer A in addition to 105 mg (0.26 mmol, 56%) of the more polar, major diastereomer B. 1H NMR (diastereomer A; 200 MHz, CDCl3): 1.37 (s,3H), 1.38 (s,3H), 1.45 (s,9H), 2.51 (d,13 Hz,1H), 2.79 (d,13 Hz,1H), 3.80 (m,2H), 4.78 (m,1H), 4.95 (br s,1H), 7.14 (m,2H), 7.59 (m,2H), 7.93 (m,1H), 8.18 (br s,1H). FAB-MS: calculated for C19H27N3O5S 409; found 410 (M+H,29%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. dissolutionThe residue was redissolved in chloroform
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by flash chromatography on silica
  8. washeluting with ethyl acetate
  9. customafforded 47 mg (0.12 mmol, 25%) of the less polar, minor diastereomer A
  10. additionin addition to 105 mg (0.26 mmol, 56%) of the more polar, major diastereomer B

Quellen und Nachweise

ORD-Eintrag
ord-4f1d50ba463e49edb46447dfcde3d1d4
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05206235

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