Ethyl Acetate → HCID 54063763, compound

HRID 654058Notes

Reaction equation

HRID 654058 reaction equation
Cl.[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH:15]([OH:28])[C@@H:16]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[NH2:17])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OCC)(=O)C.[OH-].[Na+]>O>[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH:15]([OH:28])[C@@H:16]([C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[NH2:17])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67911841HCID 67911841, compound

Product 1

HCID 54063763HCID 54063763, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of benzyl N5 -benzyloxycarbonyl-3-hydroxyornithinate hydrochloride containing approx. 90% less-soluble diastereoisomer and approx. 10% more-soluble diastereoisomer (1.0 g, 2.4 mmol) in water (15 ml) was stirred with ethyl acetate (150 ml) and adjusted to pH 7.75 with a dilute solution of sodium hydroxide. The aqueous layer was separated and extracted with ethyl acetate (3×100 ml). The combined organic layers were dried (MgSO4) and evaporated to yield benzyl N5 -benzyloxycarbonyl-3-hydroxyornithinate (0.57 g) as a partially crystalline oil. A sample of this material (430 mg, 1.15 mmol) was dissolved in distilled acetonitrile (15 ml) containing acrylic acid (0.788 ml, 11.5 mmol) and stirred at room temperature for three days. The resulting white precipitate was filtered off and washed with a few milliliters of acetonitrile to provide benzyl N2 -(β-carboxyethyl)-N5 -benzyloxycarbonyl-3-hydroxyornithinate (390mg 76%), m.p. 153.5-154.5 (acetonitrile), δmax (KBr) 3336, 1740, 1691, 1633, 1533, 750 and 698cm-1 ; δH [(CD3)2SO; 250 MHz] 1.45 (1H, m), 1.73 (1H, m), 2.31 (2H, t, J 6.6 Hz), 2.56 (1H, m), 2.74 (1H, m), 3.06 (3H, m), 3.37 (2H, br s), 3.63 (1H, m), 5.00 (2H, s), 5.12 (2H, s), 7.19 (1H, t, J 5.3 Hz) and 7.35 (10H, m). (Found: C, 61.86; H, 6.18; N, 6.21%; MH+, (p.i. F.A.B., thioglycerol), 445. C23H28N2O7 requires C, 62.15; H, 6.35; N, 6.30%; M, 444).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3215db9dfe644e29b6603f607164ff3c
Source dataset
uspto-grants-1992_07
Patent number
US05130241

Reaction notes

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