Acetic Acid → HCID 58117095, compound

HRID 2066530Notes

Reaction equation

HRID 2066530 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:17])[CH2:15]Cl)[C@@H:10]([CH2:18][OH:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].CC(O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C@@H:10]([CH2:18][O:19][CH2:15][C:14]2=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23665647Potassium tert-butoxideHCID 58117063HCID 58117063, compound

Product 1

HCID 58117095HCID 58117095, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-4-(2-chloro-acetyl)-3-hydroxymethyl-piperazine-1-carboxylic acid tert-butyl ester (710 mg, 2.45 mmol) in THF (16 mL) at 0° C. was added potassium tert-butoxide (326 mg, 2.91 mmol). The resulting mixture was stirred for 75 min before the addition of AcOH (0.6 mL). The resulting mixture was partitioned between water and DCM and the aqueous layer extracted with further DCM. The combined organic fractions were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography to give the title compound as a colourless oil (570 mg, 91%).

Workup

  1. customThe resulting mixture was partitioned between water and DCM
  2. extractionthe aqueous layer extracted with further DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-ab3557a7f4004e3ca9dadb79dc0f6fb9
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

Loading…