Hydrochloric Acid → HCID 59627130, compound

HRID 1926701Notes

Reaction equation

HRID 1926701 reaction equation
[NH2:1][C@H:2]1[CH2:11][C:10]2[C:5](=[N:6][CH:7]=[C:8]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=2)[N:4]([OH:19])[CH2:3]1.Cl.CC[O:23]CC>>[NH2:1][C@H:2]1[CH2:11][C:10]2[C:5](=[N:6][CH:7]=[C:8]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=2)[N:4]([OH:19])[C:3]1=[O:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86649300HCID 86649300, compound

Product 1

HCID 59627130HCID 59627130, compoundYield 61%

Procedure

(3S)-3-Amino-1-hydroxy-6-phenoxy-3,4-dihydro-1,8-naphthyridin-2(1H-one (67) tert-Butyl {(3S)-1-[(tert-butoxycarbonyl)oxy]-2-oxo-6-phenoxy-1,2,3,4-tetrahydro-1,8-naphthyridin-3-yl}carbamate (66) (240 mg, 0.509 mmol) was treated with a solution of HCl in Et2O (2 M, 2 mL) and allowed to stir at RT for 66 h. The solvent was removed under reduced pressure, and the residue was dissolved in a solution of 1:4 (1:9 NH4OH: CH3OH): dichloromethane (0.5 mL). This solution was subjected to silica gel chromatography (Eluant: 1:4 (1:9 NH4OH: CH3OH): dichloromethane) to provide the product as a white solid (83 mg, 61%). LCMS m/z 272.0 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.98 (br dd, J=15, 14 Hz, 1H), 3.18 (dd, J=15.3, 6.2 Hz, 1H), 4.01 (dd, J=13.8, 6.1 Hz, 1H), 7.03-7.07 (m, 2H), 7.17 (br t, J=7.4 Hz, 1H), 7.40 (dd, J=8.5, 7.5 Hz, 2H), 7.44-7.46 (m, 1H), 8.00 (br d, J=2 Hz, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in a solution of 1:4 (1:9 NH4OH: CH3OH)

Sources & evidence

ORD record
ord-31794416a9e34e1fb43b460e698fbd50
Source dataset
uspto-grants-2012_05
Patent number
US08183238B2

Reaction notes

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