Hydrochloric Acid → HCID 22855680, compound

HRID 129990Notes

Reaction equation

HRID 129990 reaction equation
C[O:2][C:3](=[O:33])[C@@H:4]([CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@H:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[NH:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10].[OH-].[Na+].Cl>CO>[N:11]1([C:9]([NH:8][C@H:7]([C:6]([NH:5][C@@H:4]([C:3]([OH:33])=[O:2])[CH2:23][C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:26][CH:25]=2)=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22855681HCID 22855681, compound

Product 1

HCID 22855680HCID 22855680, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in (3) (1.29 g) was dissolved in methanol (5.0 ml) and 1N NaOH (3.1 ml) was added at 0°~5° C. Then the reaction mixture was stirred at room temperature for 2 h. 1N HCl (3.1 ml) was added to the mixture and the resulting mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate. The solution was washed with 1N HCl and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from methanol (5 ml)/ethyl acetate (30 ml)/hexane (60 ml) to give the product (0.97 g) as colorless crystals.

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 1N HCl and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from methanol (5 ml)/ethyl acetate (30 ml)/hexane (60 ml)

Sources & evidence

ORD record
ord-edd2998d63e9444dad04538faae7a844
Source dataset
uspto-grants-1995_11
Patent number
US05470833

Reaction notes

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