Hydrochloric Acid → HCID 86725252, compound

HRID 2208575Notes

Reaction equation

HRID 2208575 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][C:26]([O:28]C)=[O:27])[CH:13]=[CH:14][C:15]=1[CH2:16][NH:17]C(OC(C)(C)C)=O)=O)(C)(C)C.[OH-].[Na+].Cl>CO.C1COCC1>[NH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][C:26]([OH:28])=[O:27])[CH:13]=[CH:14][C:15]=1[CH2:16][NH2:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86725253HCID 86725253, compound

Product 1

HCID 86725252HCID 86725252, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The methyl 2-(3,4-bis((tert-butoxycarbonylamino)methyl)phenyl)acetate (1.1 g,) was dissolved in a mixture of MeOH/THF (50 mL, 2:1). 1N NaOH (10 mmol, 10 mL) was added and the reaction mixture was stirred at room temperature overnight. 1N HCl was added to adjust the pH of the reaction to ˜3. The aqueous was extracted with EtOAc. The organic phase was washed with 1N HCl, brine, dried and concentrated in vacuo to afford the product (0.38 g) as yellow solid.

Workup

  1. customthe pH of the reaction to ˜3
  2. extractionThe aqueous was extracted with EtOAc
  3. washThe organic phase was washed with 1N HCl, brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40b1c4637af8483baf42c22095406611
Source dataset
uspto-grants-2016_06
Patent number
US09376454B2

Reaction notes

Loading…