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

HRID 446969Notes

Reaction equation

HRID 446969 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:33])[CH:18]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:6]12)=[O:4].[OH-].[Na+]>CO>[C:29]([O: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:33])=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 672807304-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 672816954-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 28 (1.1 g, 2.3 mmol) in MeOH (20 mL) was treated with 1M NaOH (10 mL) at ambient temperature. After 40 min, the solution was concentrated, acidified with 1M HCl until pH˜2, and extracted with EtOAc. The organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 29 (1.0 g) as a light yellow-colored foam which was used without further purification. 1H NMR (CDCl3, 300 MHz): δ5.23 (d, J=9.0 Hz, 1H), 4.71 (d, J=6.3 Hz, 1H), 4.33-4.16 (m, 2H), 4.16-4.06 (m, 2H), 3.82-3.78 (m, 1H), 3.73-3.66 (m, 2H), 3.17 (m, 1H), 2.92 (s, 3H), 2.66 (dd, J=5.1, 13.5 Hz, 1H), 2.13 (m, 1H), 1.77-1.55 (m, 6H), 1.43 (s, 9H), 1.29-1.01 (m, 6H) ppm.

Workup

  1. concentrationthe solution was concentrated
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a5e1a1da39c244c1b7566a08dbf9f43f
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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