Hydrochloric Acid → HCID 22855680, compound

HRID 2295172Notes

Reaction equation

HRID 2295172 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-d6c751fcf8404caab737c1b5eb92bbca
Source dataset
uspto-grants-1997_11
Patent number
US05691315

Reaction notes

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