Hydrochloric Acid → HCID 68863930, compound

HRID 1725919Notes

Reaction equation

HRID 1725919 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[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=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[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=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:12])=[O:13])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68863559HCID 68863559, compound

Product 1

HCID 68863930HCID 68863930, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 149A (0.60 g, 1.50 mmol) in methanol (16 mL) and distilled water (1.8 mL) was treated with lithium hydroxide monohydrate (0.19 g, 4.50 mmol), heated to 60° C. for four days, cooled to room temperature treated with 1N HCl, and extracted with ethyl acetate (2×). The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(−)) m/e 384 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 14.25 (br s, 1H), 9.38 (br s, 1H), 8.06 (d, 1H), 7.94 (dd, 1H), 7.80 (m, 3H), 7.72 (dt, 1H), 7.66 (d, 1H), 7.62 (dd, 1H), 7.54 (dt, 2H), 3.81 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d577783efa04f8f97a456b66f21543c
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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