Sodium Hydroxide → HCID 13863922, compound

HRID 1732140Notes

Reaction equation

HRID 1732140 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:23]([CH2:24][C:25]([O:27]C)=[O:26])[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[C@H:23]([CH2:24][C:25]([OH:27])=[O:26])[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13375568HCID 13375568, compound

Product 1

HCID 13863922HCID 13863922, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.87 g of methyl (3S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-β-carboline-3-acetate is dissolved in 12 ml of tetrahydrofuran, and 5 ml of 1N NaOH are added thereto. The mixture is stirred at room temperature for 16 hours. The mixture is evaporated to remove the solvent. The residue is dissolved in water, and the aqueous solution is extracted with ethyl acetate. The aqueous layer is acidified with 10% HCl, and extracted with ethyl acetate. The extract is washed with a saturated aqueous sodium chloride solution, dried and then evaporated to remove the solvent. 630 mg of (3S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-β-carboline-3-acetic acid are obtained as pale yellow powder. Yield: 75%

Workup

  1. customThe mixture is evaporated
  2. customto remove the solvent
  3. dissolutionThe residue is dissolved in water
  4. extractionthe aqueous solution is extracted with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with a saturated aqueous sodium chloride solution
  7. customdried
  8. customevaporated
  9. customto remove the solvent

Sources & evidence

ORD record
ord-b4e036cab67a41409dff0fc3079a3d6a
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

Loading…