Sodium Hydroxide → HCID 67237769, compound

HRID 1879576Notes

Reaction equation

HRID 1879576 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@:11]1([C:25]([O:27]C(C)(C)C)=[O:26])[CH2:16][C:15](=[O:17])[C@@H:14]2[C@H:12]1[C@H:13]2[C:18]([O:20]C(C)(C)C)=[O:19])=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCCC1.C(O)C>[C:3]([O:7][C:8]([NH:10][C@@:11]1([C:25]([OH:27])=[O:26])[CH2:16][C:15](=[O:17])[C@@H:14]2[C@@H:12]1[C@H:13]2[C:18]([OH:20])=[O:19])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59712878Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-, 2,6-bis(1,1-dimethylethyl) ester, (1S,2S,5R,6R)-

Product 1

HCID 67237769HCID 67237769, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Add 2.5M sodium hydroxide (15.55 mL, 38.88 mmol) to a stirred solution of the ditert-butyl (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (2.0 g, 4.86 mmol) in tetrahydrofuran (24.3 mL) and ethanol (9.72 mL). Heat the reaction mixture to 60° C. and maintain stirring overnight. Continue heating for 4 hours then wash with ethyl acetate. Cool the aqueous phase in an ice bath and acidify to pH=2-3 with 1N hydrochloric acid solution. Extract with ethyl acetate (3 times), dry the organic on sodium sulfate, filter and concentrate to give the title compound as an orange solid (1.4 g, 96%). MS (m/z): 322 (M+23).

Workup

  1. temperaturemaintain
  2. temperatureContinue heating for 4 hours
  3. washthen wash with ethyl acetate
  4. temperatureCool the aqueous phase in an ice bath
  5. extractionExtract with ethyl acetate (3 times)
  6. customdry the organic on sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-6f0a52df4d4247c0a0ada3f8fb571434
Source dataset
uspto-grants-2012_11
Patent number
US08318184B2

Reaction notes

Loading…