Water → (S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamate

HRID 464827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 464827
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][C@@H:10]([C:19]([OH:21])=O)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].P(C#N)(=O)(OCC)OCC.C(N(CC)CC)C.O>CN(C)C=O>[C:15]([O:14][C:12]([NH:11][C@@H:10]1[C:19](=[O:21])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH2:9]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 18599735(S)-3-(2-aminophenoxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Produkt 1

HCID 18599719(S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamateAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 120 ml of N,N-dimethylformamide is dissolved 21.4 g of O-(o-aminophenyl)-Boc-L-serine obtained in Example 2, and 14 g of diethyl phosphorocyanidate is added dropwise to the solution with stirring at ice bath temperature. The mixture is stirred for 10 minutes, and 7 g of triethylamine is added dropwise to the mixture. After stirring for 1 hour, the mixture is poured in ice-cooled water. The deposited material is collected by filtration, washed with water, dried and recrystallized from ethyl acetate-hexane to give 12.3 g of 3(S)-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1,5-benzoxazepine-4-one as colorless plates, melting at 202°-203° C.

Aufarbeitung

  1. additionis added dropwise to the solution
  2. stirringThe mixture is stirred for 10 minutes
  3. stirringAfter stirring for 1 hour
  4. additionthe mixture is poured in ice-
  5. filtrationThe deposited material is collected by filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-abf5c0e0beaa4f7d93ec516445c119a3
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04548932

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