HCID 21302823, compound → HCID 21302822, compound

HRID 1061656Notes

Reaction equation

HRID 1061656 reaction equation
Cl.C(OCC)(=O)C.[CH:8]([NH:11][C:12](=[O:31])[CH:13]([OH:30])[C@@H:14]([NH:22]C(OC(C)(C)C)=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:10])[CH3:9]>>[CH:8]([NH:11][C:12](=[O:31])[CH:13]([OH:30])[C@@H:14]([NH2:22])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 21302823HCID 21302823, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 21302822HCID 21302822, compound

Procedure

A 4 M hydrogen chloride/ethyl acetate solution (2 ml) is added to N1-isopropyl-(2RS,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutyramide (300 mg, Reference compound No. 20-1), and the mixture is stirred for five hours. The reaction mixture is concentrated under reduced pressure, a saturated aqueous sodium hydrogencarbonate solution is added to the resulting residue, and the whole is extracted with ethyl acetate. The extract is washed with water and saturated brine successively and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure to give the titled reference compound (212 mg).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogencarbonate solution is added to the resulting residue
  3. extractionthe whole is extracted with ethyl acetate
  4. washThe extract is washed with water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe extract is concentrated under reduced pressure

Sources & evidence

ORD record
ord-341df01613cb43438bde6f9998e23da1
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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