Sodium Hydroxide → HCID 86725252, compound

HRID 1478842Notes

Reaction equation

HRID 1478842 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+]>CO.C1COCC1.Cl>[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 2

HCID 14798Sodium HydroxideHCID 86725253HCID 86725253, compound

Product 1

HCID 86725252HCID 86725252, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 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. IN HCl was added to adjust the pH of the reaction to ˜3. The aqueous was extracted with EtOAc. The organic phase was washed with IN 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 IN HCl, brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e551fdf7d11c42dfa9e2959eae81452a
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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