Hydrochloric Acid → Ethyl 10-amino-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate

HRID 1093077Notes

Reaction equation

HRID 1093077 reaction equation
C(OC([NH:11][C:12]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][N:14]1[C:21](=[O:31])[C:22]([OH:30])=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:24]=[C:13]21)=O)C1C=CC=CC=1.Cl.[H][H]>C(O)C.[Pd]>[NH2:11][C:12]12[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20]1)[CH2:15][N:14]1[C:21](=[O:31])[C:22]([OH:30])=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:24]=[C:13]21

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 57904801Ethyl 10-(((benzyloxy)carbonyl)amino)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57905130Ethyl 10-amino-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylateYield 102%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of ethyl 10-(((benzyloxy)carbonyl)amino)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate (2 g, 4.68 mmol) in ethanol (75 mL) was added 1N HCl (5.15 mL, 5.15 mmol) followed by Pd/C (0.498 g, 0.468 mmol) and the mixture stirred under 1 atm of hydrogen for 18 h. The mixture was then filtered through a pad of CELITE® and the pad washed with dichloromethane. The filtrate was then concentrated to afford the title compound (1.4 g, 91% yield) as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ: 10.5 (1 H, brs), 4.3 (2 H, q, J=7.02 Hz), 4.0 (2 H, d, J=3.66 Hz), 2.4 (1 H, brs), 2.0-2.1 (4 H, m), 1.8-1.9 (2 H, m), 1.7-1.8 (2 H, m), 1.3 (3 H, t, J=7.02 Hz). LCMS (M+H)=294.32.

Workup

  1. filtrationThe mixture was then filtered through a pad of CELITE®
  2. washthe pad washed with dichloromethane
  3. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-b00cd4f75f284452b98190e09da59203
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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