Water → 3-(Benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylic acid

HRID 1365743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1365743
[CH2:1]([O:8][C:9]1[C:21](=[O:22])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][C:18]([CH3:20])([CH3:19])[C:12]2=[N:11][C:10]=1[C:23]([O:25]CC)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].O>C1COCC1>[CH2:1]([O:8][C:9]1[C:21](=[O:22])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][C:18]([CH3:20])([CH3:19])[C:12]2=[N:11][C:10]=1[C:23]([OH:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58877852Ethyl 3-(benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylate

Produkt 1

HCID 588778933-(Benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylic acidAusbeute 91,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 3-(benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylate (920 mg, 2.5 mmol) was dissolved in 5 mL of THF and to it was added with stirring LiOH (120 mg, 5 mmol) and 5 mL water. After 30 min, the THF was evaporated and the aqueous layer was acidified with dil HCl. This was extracted with CH2Cl2, dried (MgSO4), filtered and concentrated. Trituration from Et2O gave the title compound (790 mg, 91%) as a solid: 1H NMR (300 MHz, CDCl3) δ: 1.40 (s, 6H), 3.60 (s, 2H), 3.65-3.95 (m, 2H), 4.10-4.90 (m, 2H), 5.41 (s, 2H), 7.25-7.42 (m, 3H), 7.45-7.58 (m, 2H). LC/MS (M+H): 345.

Aufarbeitung

  1. customthe THF was evaporated
  2. extractionThis was extracted with CH2Cl2
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-23ac3ebecc414ddf801866527fd2dd2b
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893055B2

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