Trifluoroacetic acid → (3S, 6R)-3-aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one
Reaction equation
C(OC([NH:8][C@H:9]1[CH2:15][CH2:14][C@@H:13]([O:16][C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[CH2:12][NH:11][C:10]1=[O:25])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C@H:9]1[CH2:15][CH2:14][C@@H:13]([O:16][C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[CH2:12][NH:11][C:10]1=[O:25]Participants
Procedure
To a solution of (3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl) oxy-2H-azepin-2-one (10 g, 28.2 mmol) in 40 mL of CH2Cl2 is added TFA (25 mL) at room temp., and the reaction solution is stirred at room temp. for 1 hr, then concd via rotary evaporation (bath temp<20° C.). The residue is diluted with CH2Cl2 (100 mL), and washed with NH4OH (10 mL) and then water (2×20 mL) and dried (Na2SO4). The reaction mixture is adsorbed on silica and chromatographed (5% methanol-CH2Cl2) to give 6.0 (85.0%) of (3S, 6R)-3-aminohexahydro-6-(cyclohexanecarbonyl)oxy-2H-azepin-2-one as a white solid: 1H NMR (CDCl3): δ 6.91 (s, 1H), 4.91 (s, 1H), 4.39 (s, 2H), 3.87 (d, J=9.8 Hz, 1H), 3.48 (t, J=6.02 Hz, 1H), 3.43 (dd, J=15.45Hz and 4.90 Hz, 1H), 2.30 (tt, J=10.92 Hz and 3.39 Hz, 1H), 2.13 (m, 1H), 1.91 (m, 4H), 1.73 (m, 2H), 1.65 (m, 1H), 1.40 (q, J=11.68 Hz, 4H), 1.24 (m, 2H).
Workup
- customconcd via rotary evaporation (bath temp<20° C.)
- additionThe residue is diluted with CH2Cl2 (100 mL)
- washwashed with NH4OH (10 mL)
- dry with materialwater (2×20 mL) and dried (Na2SO4)
- customchromatographed (5% methanol-CH2Cl2)
Sources & evidence
- ORD record
- ord-6f9e3f1490784d1fbcd24a662bf465b7
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06239127B1
Reaction notes
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