Hydrochloric Acid → HCID 11494819, compound

HRID 1725955Notes

Reaction equation

HRID 1725955 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:13])=[O:12])=[O:4].O.O.[OH-].[Li+].Cl>CO>[CH3:28][O:27][C:25]([C:16]1[C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=2[CH:23]=[CH:24][C:15]=1[NH:14][S:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]([OH:4])=[O:2])(=[O:13])=[O:12])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 11668533HCID 11668533, compound

Product 1

HCID 11494819HCID 11494819, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 379A (3.04 g, 7.54 mmol) in methanol (70 mL) and distilled water (7.8 mL) was treated with lithium hydroxide monohydrate (1.58 g, 37.7 mmol), heated to 60° C. overnight, cooled to room temperature, treated with 1N HCl, and concentrated. The aqueous layer was washed with dichloromethane two times and the combined organic phases were dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 388 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 14.00 (br s, 1H), 8.85 (br s, 1H), 7.83 (d, 1H), 7.73 (m, 2H), 7.64 (m, 1H), 7.13 (s, 2H), 3.63 (s, 3H), 2.67 (br s, 2H), 2.51 (br s, 2H), 1.65 (br m, 4H).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. washThe aqueous layer was washed with dichloromethane two times
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c57c930ef63b408ea47be499284468f6
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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