Hydrochloric Acid → HCID 21309709, compound

HRID 617313Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2C(OC(C)(C)C)=O)[CH:5]=[N:6][CH:7]=1.[ClH:21]>>[ClH:1].[ClH:21].[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][NH:11]2)[CH:5]=[N:6][CH:7]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 10780459HCID 10780459, compound

Product 1

HCID 21309709HCID 21309709, compoundYield 80%

Procedure

The compound from step 39a (0.130 g, 0.44 mmol) was treated with saturated ethanolic HCl (5 mL) for 16 hr. The volatiles were removed in vacuo, and the dihydrochloride was recrystallized (EtOH/Et2O) to yield the title compound (0.094 g, 80%) as a white solid. mp 158-157° C. MS (DCI/NH3) m/e: 199 (M+H)+, 216 (M+NH4)+. 1H NMR (D2O, 300 MHz) d: 8.41 (d, J=5.1 Hz, 1H), 8.39 (d, J=4.4 Hz, 1H), 7.94 (t, J=2.1 Hz, 1H), 5.01-4.93 (m, 1H), 4.50 (d, J=4.0 Hz, 2H), 4.20-4.03 (m, 2H), 2.69 (q, J=8.45 Hz, 2H). Anal. calc. for C9H13Cl3N2O.0.5H2O: C, 38.53; H, 5.03; N, 9.98 Found: C, 38.51; H, 5.16 N, 9.96. [α]D23 =-3.23° (c=0.16 in MeOH).

Workup

customThe volatiles were removed in vacuo
customthe dihydrochloride was recrystallized (EtOH/Et2O)

Sources & evidence

ORD record: ord-3d2811526e7246bdaaa18e89fc8b613c
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948793

Reaction notes

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