Ethanol → HCID 66782861, compound

HRID 1096295Notes

Reaction equation

HRID 1096295 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C@@H:14]([OH:18])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:24][CH2:25]O>>[CH2:24]([O:16][C:15](=[O:17])[C@H:14]([OH:18])[CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:25]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7004002(R)-4-(((Benzyloxy)carbonyl)amino)-2-hydroxybutanoic acid

Product 1

HCID 66782861HCID 66782861, compoundYield 81%

Procedure

A solution of (R)-4-benzyloxycarbonylamino-2-hydroxy-butyric acid (2.42 g, 9.56 mmol) and sulfuric acid (94 mg, 0.96 mmol) in EtOH (6 mL) was heated at reflux for 18 h, then partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated to afford the title compound (2.18 g, 81%). Light yellow liquid, MS: 304.2 (M+Na)+.

Workup

  1. temperatureat reflux for 18 h
  2. custompartitioned between EtOAc and sat. aq. NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8fc82388e0f34039811990c1957635ff
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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