Sodium Hydroxide → 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid

HRID 446981Notes

Reaction equation

HRID 446981 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][N:8]([C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])[CH:7]2[CH2:15][CH2:16][N:17]([C:18](=[O:34])[CH:19]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:6]12)=[O:4].[OH-].[Na+]>CO>[C:30]([O:29][C:27]([NH:26][CH:19]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C:18]([N:17]1[CH:6]2[CH:7]([N:8]([C:10]([CH:12]3[CH2:13][CH2:14]3)=[O:11])[CH2:9][CH:5]2[C:3]([OH:4])=[O:2])[CH2:15][CH2:16]1)=[O:34])=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 672823014-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 672806544-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acidYield 109.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 44 (580 mg, 1.21 mmol) in MeOH (20 mL) was treated with 1M NaOH (4 mL) at ambient temperature. After 4 h, the solution was concentrated and diluted with EtOAc and 1M HCl. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed successively with 1M HCl, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 45 (613 mg) as a yellow-colored foam which was used without further purification. Mass spectrum, m/z [464.6] (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with EtOAc and 1M HCl
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic extracts were washed successively with 1M HCl, and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ebfc484d18ba42c5a005b916bbe3611a
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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