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Hydrochloric Acid → (+)-3(R)-(2(R)-Amino-3-phenylpropionylamino)-5-cyclohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

HRID 743702
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 743702
C(OC([NH:8][C@H:9]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:10]([NH:12][CH:13]1[N:19]=[C:18]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH3:30])[C:14]1=[O:31])=[O:11])=O)(C)(C)C.Cl>C(OCC)(=O)C>[NH2:8][C@H:9]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:10]([NH:12][C@@H:13]1[N:19]=[C:18]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH3:30])[C:14]1=[O:31])=[O:11]
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 1317187683(R,S)-[2(R)-(tert-Butyloxycarbonvl)amino-3-phenylpropionylamino]-5-cyclohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

Produkt 1

HCID 18656026(+)-3(R)-(2(R)-Amino-3-phenylpropionylamino)-5-cyclohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-oneAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3(R,S)-[2(R)-(tert-Butyloxycarbonyl)amino-3-phenylpropionylamino]-5-cyclohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (4.7 g) was dissolved in ethyl acetate (20 ml) and cooled to 0° C. This solution was then saturated with hydrogen chloride gas. After 1.5 h, the resulting precipitate (which was shown to be the undesired diastereoisomer, Rf=0.04 ethyl acetate), was removed by filtration and the filtrate evaporated. The solid residue was partitioned between ethyl acetate (25 ml) and 10% sodium carbonate solution (20 ml). The organic phase was separated and the aqueous extracted with ethyl acetate (2×25 ml). The combined organic phases were dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel using a gradient elution of 0-20% methanol in ethyl acetate to afford the title compound (1.66 g). Mp 100°-103° C. 1H NMR (360 MHz, CDCl3) δ 1.00-1.39 (4H, m), 1:50-1.72 (4H, m), 1.84-1.92 (1H, m), 2.00-2.07 (1H, m), 2.72-2.84 (2H, m), 3.28 (1H, dd, J=13.8 and 4.0 Hz), 3.40 (3H, s), 3.69 (1H, dd, J=9.8 and 4.1 Hz), 5.36 (1H, d, J=8.3 Hz), 7.21-7.36 (7H, m), 7.47-7.58 (2H, m), 8.66 (1H, d, J=8.3 Hz). [α]D23 +32.7° (c=0.58, CH3OH).

Aufarbeitung

  1. customwas removed by filtration
  2. customthe filtrate evaporated
  3. customThe solid residue was partitioned between ethyl acetate (25 ml) and 10% sodium carbonate solution (20 ml)
  4. customThe organic phase was separated
  5. extractionthe aqueous extracted with ethyl acetate (2×25 ml)
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel using
  9. washa gradient elution of 0-20% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f5f53e37b4f545f9be6fdb2de5a6b74a
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05556969

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