Sodium Hydroxide → HCID 86722979, compound

HRID 1404373Notes

Reaction equation

HRID 1404373 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:9]1[CH2:12][CH:11]([CH2:13][C:14]([O:16]C)=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([O:5][C:6]([N:8]([CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:9]1[CH2:12][CH:11]([CH2:13][C:14]([OH:16])=[O:15])[CH2:10]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86722977HCID 86722977, compound

Product 1

HCID 86722979HCID 86722979, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To methyl 2-(3-(tert-butoxycarbonyl(2-(tert-butoxycarbonylamino)ethyl)amino)cyclobutyl)acetate from step 2 in a mixture of MeOH and H2O was added 1N NaOH (8 mL). The resultant reaction mixture was stirred at RT overnight. Half of the solvents were removed under reduced pressure and 1N HCl was added to adjust pH of the solution to 4. The aqueous phase was extracted with EtOAc for three times. The combined organic phase was then dried and concentrated in vacuo to afford the acid (0.9 g).

Workup

  1. customThe resultant reaction mixture
  2. customHalf of the solvents were removed under reduced pressure and 1N HCl
  3. additionwas added
  4. extractionThe aqueous phase was extracted with EtOAc for three times
  5. customThe combined organic phase was then dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-489193c7c9874db5a3d5287fc3933b8a
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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