Sodium Carbonate → n-boc-2-(indole-3-yl)-dl-glycine

HRID 2420012Notes

Reaction equation

HRID 2420012 reaction equation
C([O:5][C:6](=[O:25])[CH:7]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)CCC.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[C:21]([O:20][C:18]([NH:17][CH:7]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[C:6]([OH:25])=[O:5])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 53919156HCID 53919156, compound

Product 1

HCID 2756803n-boc-2-(indole-3-yl)-dl-glycine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 5.9 g. (0.017 mol.) of the ester in 70 ml. of 5% aqueous sodium carbonate and 30 ml. of dioxane was refluxed for 2.5 hours. The cooled reaction mixture was concentrated in vacuo and 30 ml. of water was added to the residue. The aqueous solution was extracted with methylene chloride, cooled and acidified to pH 2.0 with hydrochloric acid. The resulting solid was collected and recrystallized from ethyl acetate-hexane to give the title compound, m.p. 143.5°.

Workup

  1. additionA suspension of 5.9 g
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo and 30 ml
  4. additionof water was added to the residue
  5. extractionThe aqueous solution was extracted with methylene chloride
  6. temperaturecooled
  7. customThe resulting solid was collected
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1f12ad28fe604443b7fb5585c0fb321a
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

Loading…