Water → HCID 86722982, compound

HRID 1404376Notes

Reaction equation

HRID 1404376 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[O:27][CH3:28])[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].C1COCC1.O.[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[O:27][CH3:28])[CH:9]1[CH2:12][CH:11]([CH2:13][C:14]([OH:16])=[O:15])[CH2:10]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86722981HCID 86722981, compound

Product 1

HCID 86722982HCID 86722982, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 2-(3-(tert-butoxycarbonyl(2,4-dimethoxybenzyl)amino)cyclobutyl)acetate from step 2 in a mixture of MeOH, THF and H2O was added 1N NaOH (10 mL). The resultant reaction mixture was stirred at RT for 2 hr. Half of the solvents were removed under reduce 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 (0.67 g).

Workup

  1. customThe resultant reaction mixture
  2. customHalf of the solvents were removed
  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-42ddb0b092b245aabf88697caefe1729
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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