Sodium Hydroxide → HCID 135741236, compound

HRID 1053820Notes

Reaction equation

HRID 1053820 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=1)=[NH:10])=[O:7])([CH3:4])[CH3:3].[OH-].[Na+]>CO>[CH3:4][C:2]([O:5][C:6]([NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=1)=[NH:10])=[O:7])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135743590methyl 4-(N-(tert-butoxycarbonyl)carbamimidoyl)benzoate

Product 1

HCID 135741236HCID 135741236, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound prepared in Example 17 (0.20 g, 0.72 mmol) in methanol (10 mL) was added 1 M aqueous sodium hydroxide (5 mL). The reaction was stirred at room temperature for 1 h. The mixture was concentrated and the resulting aqueous residue was diluted with ethyl acetate. The aqueous layer was acidified with 1 M hydrochloric acid to pH 4-5 and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried and concentrated to give the title compound (0.208 g, >99%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe resulting aqueous residue was diluted with ethyl acetate
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fba6974f0f2b422f81bda3cb43b3af30
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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