Sodium Hydroxide → HCID 67640213, compound

HRID 399525Notes

Reaction equation

HRID 399525 reaction equation
[C:1]([O:5][C:6](=[O:31])[C@@H:7]1[CH2:11][C@H:10]([O:12]C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH2:9][N:8]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.C(O)(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:31])[C@@H:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][N:8]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67639590HCID 67639590, compound

Product 1

HCID 67640213HCID 67640213, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (4S)-1-(tert-butyloxycarbonyl)-4-(p-nitrobenzoyloxy)-L-proline tert-butyl ester (575 mg, 1.32 mmol) in ethanol (13 mL) was treated with 0.4N sodium hydroxide (4.3 mL, 1.72 mmol) for 18 hours at room temperature. The solution was neutralized with several drops of glacial acetic acid, diluted with ethyl acetate (100 mL), washed with water (2×), saturated brine solution, dried (Na2SO4), and evaporated. The residue was subjected to flash silica gel chromatography eluting with 5% acetone/dichloromethane. The title compound (313 mg) was obtained contaminated with some p-nitrobenzoic acid and used without further purification in the next step.

Workup

  1. washwashed with water (2×), saturated brine solution
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. washeluting with 5% acetone/dichloromethane

Sources & evidence

ORD record
ord-698172668052422f89f09be4dc7c0425
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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