Hydrochloric Acid → HCID 86610317, compound

HRID 1865808Notes

Reaction equation

[CH3:1][S:2]([O:5][CH:6]([CH3:41])[CH2:7][N:8]([CH2:33][CH:34]([O:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH3:35])[C:9]1[C:14]([C:15]([NH:17][CH2:18][CH2:19][O:20]C2CCCCO2)=[O:16])=[CH:13][C:12]([N+:27]([O-:29])=[O:28])=[CH:11][C:10]=1[N+:30]([O-:32])=[O:31])(=[O:4])=[O:3].Cl>C1COCC1.O>[CH3:40][S:37]([O:36][CH:34]([CH3:35])[CH2:33][N:8]([CH2:7][CH:6]([O:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH3:41])[C:9]1[C:10]([N+:30]([O-:32])=[O:31])=[CH:11][C:12]([N+:27]([O-:29])=[O:28])=[CH:13][C:14]=1[C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])(=[O:39])=[O:38]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 19 (2.52 g, 4.03 mmol) in THF (150 mL) was treated with1 N HCl (100 mL), and the solution was stirred at 20° C. for 1 h, then diluted with water (100 mL), neutralized with satd. NaHCO3, and extracted with EtOAc (3×80 mL). The combined organic phases were washed with brine and dried, the solvent was evaporated, and the residue was purified by chromatography on silica gel, eluting with EtOAc/MeOH (100:1), to give 2-(2-{[(2-hydroxyethyl)amino]carbonyl}{2-[(methylsulfonyl)oxy]propyl}-4,6-dinitroanilino)-1-methylethyl methanesulfonate (20) (0.80 g, 37%): as a yellow foam; 1H NMR [(CD3)2SO] δ 8.94 (m, 1 H), 8.72 (m, 1 H), 8.35 (m, 1 H), 4.92 (m, 2 H), 3.56 (m, 2 H), 3.30 (m, 6 H), 3.16 (s, 6 H), 1.32 (m, 6 H); 13C NMR δ 165.9, 145.8, 143.4, 139.4, 133.6, 128.0, 123.1, 76.3, 59.2, 57.3, 42.2, 37.7, 18.6. HRMS (FAB) Calcd. For C17H27N4O12S2 [M+H+] m/z 543.1067. Found; 543.1074.

Workup

extractionNaHCO3, and extracted with EtOAc (3×80 mL)
washThe combined organic phases were washed with brine
customdried
customthe solvent was evaporated
customthe residue was purified by chromatography on silica gel
washeluting with EtOAc/MeOH (100:1)

Sources & evidence

ORD record: ord-1ea9b5ec32954e8ea601a05aa2ad70d9
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629332B2

Reaction notes

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