Hydrochloric Acid → HCID 67417383, compound

HRID 1429349Notes

Reaction equation

HRID 1429349 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17]C)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>[OH-].[Na+].CO>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67382092HCID 67382092, compound

Product 1

HCID 67417383HCID 67417383, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

The suspension of compound 1a (39.9 g, 100 mmol) in 3.5N aqueous NaOH (130 mL) and MeOH (350 mL) was heated to 50° C. for 3 hr. Then the mixture was cooled to rt and acidified to pH=3 with 3.5N aqueous HCl, extracted with EA (2×300 mL). The organic extracts were combined and dried over anhydrous Na2SO4, concentrated under reduced pressure to get compound 1b as a white solid (34.7 g, 90% yield). 1H NMR (400 MHz, CDCl3): δ 8.08-8.06 (m, 1H), 7.73-7.53 (m, 2H), 7.42-7.40 (m, 1H), 7.30-7.19 (m, 5H), 4.95-4.84 (m, 2H), 4.05-4.02 (m, 1H), 3.55-3.48 (m, 2H), 2.93-2.91 (m, 2H), 1.45 (s, 9H).

Workup

  1. temperatureThen the mixture was cooled to rt
  2. extractionextracted with EA (2×300 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b547ca072244d3e87355d0a885443c1
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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