Hydrochloric Acid → HCID 86725252, compound

HRID 576612Notes

Reaction equation

HRID 576612 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-efa050cbc7c4433da685772591070552
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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