Ethanol → HCID 66902295, compound

HRID 2242309Notes

Reaction equation

HRID 2242309 reaction equation
[C:1]1([C@H:7]([NH:9][C@@:10]2([C:20]([OH:22])=[O:21])[CH2:15][C@H:14]([OH:16])[CH:13]3[CH:11]2[C@H:12]3[C:17]([OH:19])=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23](Cl)(=O)[CH3:24].[CH2:27](O)[CH3:28]>>[C:1]1([C@H:7]([NH:9][C@@:10]2([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:15][C@H:14]([OH:16])[CH:13]3[CH:11]2[C@H:12]3[C:17]([O:19][CH2:27][CH3:28])=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 66902113HCID 66902113, compound

Product 1

HCID 66902295HCID 66902295, compoundYield 99%

Procedure

To a suspension of 2-[((1R)-1-phenylethyl)amino](2S,4S,6R)-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid (4 g, 13 mmol) in 48 mL of ethanol at room temperature is added acetyl chloride (11.2 mL, 157 mmol) via an addition funnel such that a gentle reflux is maintained. The resulting mixture is allowed to stir another 16 hours at reflux and upon cooling to room temperature is concentrated in vacuo to a solid residue. The solid is treated slowly with a solution of sodium bicarbonate (6.6 g) in 100 mL of water followed by washing with ethyl acetate (2×100 mL). The combined organics are dried (MgSO4), filtered, and concentrated in vacuo to give 4.7 g (99%) of the title compound as a solid. Column chromatography on silica gel eluting with CH2Cl2/MeOH (95:5) followed by crystallization from Et2O provides an analytically pure sample of the title compound as a white solid.

Workup

  1. temperaturea gentle reflux
  2. temperatureis maintained
  3. temperatureat reflux
  4. concentrationis concentrated in vacuo to a solid residue
  5. additionThe solid is treated slowly with a solution of sodium bicarbonate (6.6 g) in 100 mL of water
  6. washby washing with ethyl acetate (2×100 mL)
  7. dry with materialThe combined organics are dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2080b5630b314e84893f4cc1cecb236d
Source dataset
uspto-grants-2010_03
Patent number
US07671082B2

Reaction notes

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