Hydrochloric Acid → HCID 54498678, compound

HRID 458079Notes

Reaction equation

HRID 458079 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][CH:6]([CH2:11][P:12]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH:8]([CH3:10])[CH3:9])C.Cl>O1CCOCC1.O>[CH2:18]([O:17][P:12]([CH2:11][CH:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:5][C:4]([OH:20])=[O:3])([O:14][CH2:15][CH3:16])=[O:13])[CH3:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54362658HCID 54362658, compound

Product 1

HCID 54498678HCID 54498678, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Lactam 6 (0.64 g, 3.87 mmol) was dissolved in 1,4-dioxane (4 mL) and hydrochloric acid (16 mL of a 6N solution), and the mixture was refluxed for 6 hours. After cooling, the mixture was diluted with water (20 mL) and washed with dichloromethane (2×15 mL). The aqueous layer was evaporated under reduced pressure to give acid 7 (0.67 g, 79%) as a white solid. Recrystallization using ethyl acetate/methanol gave Example 41 exclusively (0.26 g);δH (400 MHz; d6-DMSO) 7.98 (2H, br s, NH2), 3.13 (2H, s, CH2NH2), 2.70 (2H, s), 2.17–2.14 (4H, m), 1.85 (2H, dd, J 13.3, 8.0), 1.63 (2H, m), 1.55 (2H, dd, J 12.9, 5.1); m/z (ES+) 184 (M+H, 100%); LCMS (Prodigy C18, 50 mm×4.6 mmid column, 5–50% Acetonitrile/water) Retention Time=2.40 minutes, 98% purity.

Workup

  1. temperatureAfter cooling
  2. washwashed with dichloromethane (2×15 mL)
  3. customThe aqueous layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7448048574eb47ae9a068c5d6d1db03a
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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