Hydrochloric Acid → (3RS)-3-amino-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

HRID 963463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963463
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[N:10][CH:9]([NH:25]C(OC(C)(C)C)=O)[C:8]1=[O:33])=[O:5])[CH3:2].Cl.O.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[NH2:25][CH:9]1[N:10]=[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:8]1=[O:33]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 19081166(3RS)-1-ethoxycarbonylmethyl-3-tert-butoxycarbonylamino-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Produkt 1

HCID 10066773(3RS)-3-amino-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-oneAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (3RS)-1-ethoxycarbonylmethyl-3-tert-butoxycarbonylamino-5-(2-fluorophenyl)-2,3-dihydro-1H -1,4-benzo-diazepin-2-one (7.2 g) in methanol (100 ml) was added 4N solution of hydrogen chloride in ethyl acetate (55 ml) under stirring at ambient temperature. The mixture was stirred for 4 hours under the same condition and allowed to stand overnight. The solvent was removed in vacuo to give residue, to which was added water. The mixture was adjusted to pH 8 with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate twice. The combined extract was washed with water and dried over magnesium sulfate. Removal of the solvent afford (3RS)-3-amino-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (5.46 g) as an amorphous mass, which was used in a following reaction step without further purification,

Aufarbeitung

  1. stirringThe mixture was stirred for 4 hours under the same condition
  2. customThe solvent was removed in vacuo
  3. customto give residue
  4. extractionextracted with ethyl acetate twice
  5. extractionThe combined extract
  6. washwas washed with water
  7. dry with materialdried over magnesium sulfate
  8. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-329f5d76fda342d5be24e743c8f94397
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763437

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