HCID 70130107, compound → HCID 57042100, compound

HRID 849356Notes

Reaction equation

HRID 849356 reaction equation
C([O:3][C:4]([CH2:6][N:7]([C@H:27]([CH3:50])[C@@H:28]([C:37]1[CH:42]=[CH:41][C:40]([O:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:39][CH:38]=1)[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:8]([C@@:10]1([C:22]([O:24]CC)=[O:23])[O:14][C@H:13]([C:15]([O:17]C(C)(C)C)=[O:16])[CH2:12][O:11]1)=[O:9])=[O:5])C>C(O)=O>[C:4]([CH2:6][N:7]([C@H:27]([CH3:50])[C@@H:28]([C:37]1[CH:38]=[CH:39][C:40]([O:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[CH:41][CH:42]=1)[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:8]([C@@:10]1([C:22]([OH:24])=[O:23])[O:14][C@H:13]([C:15]([OH:17])=[O:16])[CH2:12][O:11]1)=[O:9])([OH:5])=[O:3]

Participants

3

Reactant 1

HCID 70130107HCID 70130107, compound

Product 1

HCID 57042100HCID 57042100, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

310 mg of 4-tert-butyl 2-ethyl (2S*,4S)-2-[N-(ethoxycarbonylmethyl)-N-{(1R,2R)-1-methyl-2-(4-phenoxyphenyl)-4-phenylbutyl}carbamoyl]-1,3-dioxolane-2,4-dicarboxylate was dissolved in 4 ml of formic acid, followed by stirring at room temperature for 2 hours. The reaction solution was evaporated to dryness under reduced pressure, and then, the residue was dissolved in 6 ml of a 50% tetrahydrofuran aqueous solution. 3 ml of a 1N sodium hydroxide aqueous solution was added, followed by stirring at room temperature for 6 hours. The reaction solution was acidified with 1N hydrochloric acid and then extracted with ethyl ether. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by medium pressure liquid chromatography (Lobar column™, Size B, RP-8, manufactured by Merck Co.; acetonitrile/0.1% trifluoroacetic acid aqueous solution=1/1) to obtain 216 mg (yield: 84%) of the above identified compound as a colorless foam.

Workup

  1. customThe reaction solution was evaporated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in 6 ml of a 50% tetrahydrofuran aqueous solution
  3. addition3 ml of a 1N sodium hydroxide aqueous solution was added
  4. stirringby stirring at room temperature for 6 hours
  5. extractionextracted with ethyl ether
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationThe drying agent was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by medium pressure liquid chromatography (Lobar column™, Size B, RP-8, manufactured by Merck Co.; acetonitrile/0.1% trifluoroacetic acid aqueous solution=1/1)
  10. customto obtain 216 mg (yield: 84%) of the

Sources & evidence

ORD record
ord-382d2afbe1b94757aa5ae20922d70b2a
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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