Sodium Hydroxide → 4-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid

HRID 446963Notes

Reaction equation

HRID 446963 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][N:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]2[CH2:14][CH2:15][N:16]([C:17](=[O:39])[CH:18]([NH:25][C:26](=[O:38])[CH:27]([N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH3:30])[CH3:28])[CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:6]12)=[O:4].[OH-].[Na+]>CO>[C:34]([O:33][C:31]([N:29]([CH3:30])[CH:27]([CH3:28])[C:26]([NH:25][CH:18]([CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[C:17]([N:16]1[CH:6]2[CH:7]([N:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:9][CH:5]2[C:3]([OH:4])=[O:2])[CH2:14][CH2:15]1)=[O:39])=[O:38])=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 672813824-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 672809014-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 20 (362 mg, 0.63 mmol) in MeOH (10 mL) was treated with 1M NaOH (2 mL) at ambient temperature. After 1 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, brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 21 as a yellow-colored foam (278 mg) which was used without further purification.

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, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2eda79119c3e4767852841a286523225
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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