Hydrochloric Acid → HCID 18655121, compound

HRID 2226570Notes

Reaction equation

HRID 2226570 reaction equation
N#N.C(OC([NH:10][C@H:11]([C:15]([NH:17][CH:18]([C:20]1[S:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[CH:21]=1)[CH3:19])=[O:16])[CH:12]([CH3:14])[CH3:13])=O)(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[S:24]1[C:20]([CH:18]([NH:17][C:15](=[O:16])[C@H:11]([CH:12]([CH3:13])[CH3:14])[NH2:10])[CH3:19])=[CH:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86748152HCID 86748152, compound

Product 1

HCID 18655121HCID 18655121, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

11.3 g of N2 -tert-butoxycarbonyl-N1 -[1-(2-benzo[b]thienyl)ethyl]-L-valinamide was dissolved in 150 ml of ethyl acetate, and 20 ml of 6N hydrochloric acid was added to the resultant solution at room temperature. After agitating overnight at room temperature, the pH of the solution was adjusted to 7-8 with a saturated aqueous solution of sodium bicarbonate under water cooling. The ethyl acetate layer was then washed with water, dried over anhydrous magnesium sulfate, and concentrated to yield a crude product. This crude product was then refined on FLORISIL® column chromatography to yield 6.7 g of the desired product, a white solid substance (melting point: 70°-71° C.).

Workup

  1. washThe ethyl acetate layer was then washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customto yield a crude product

Sources & evidence

ORD record
ord-51a46b61577d499180b18e7ef4a9e0ad
Source dataset
uspto-grants-1994_09
Patent number
US05348976

Reaction notes

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