Hydrochloric Acid → HCID 70109999, compound

HRID 1602566Notes

Reaction equation

HRID 1602566 reaction equation
[C:1]([O:5][C:6]([C:8](=[C:14]([OH:54])[C:15](=[O:53])[N:16]([C@H:26]([CH3:52])[C@@H:27]([C:43]1[CH:48]=[CH:47][C:46]2[O:49][CH2:50][O:51][C:45]=2[CH:44]=1)[CH2:28][C:29]1[O:30][C:31]([C:34](=[O:42])[NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:32][CH:33]=1)[CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:9][C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>O1CCCC1.O>[C:1]([O:5][C:6]([C:8](=[C:14]([OH:54])[C:15](=[O:53])[N:16]([C@H:26]([CH3:52])[C@@H:27]([C:43]1[CH:48]=[CH:47][C:46]2[O:49][CH2:50][O:51][C:45]=2[CH:44]=1)[CH2:28][C:29]1[O:30][C:31]([C:34](=[O:42])[NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:32][CH:33]=1)[CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70107872HCID 70107872, compound

Product 1

HCID 70109999HCID 70109999, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

285 mg of methyl 3-(tert-butoxycarbonyl)-4-hydroxy-4-[N-[(1R,2R)-1-methyl-2-(3,4-methylenedioxyphenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-{(E)-3-phenyl-2-propenyl}carbamoyl]-3-butenoate was dissolved in a mixture of 15 ml of tetrahydrofuran and 10 ml of water and stirred together with 4 ml of 1N aqueous sodium hydroxide at room temperature for 2.5 days. The reaction solution was acidified with 1N hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [chloroform/methanol=100/1→10/1] to give 213 mg (yield: 76%) of the title compound as a colorless foamy substance.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [chloroform/methanol=100/1→10/1]

Sources & evidence

ORD record
ord-2b2bfb7d28cc4581bbfe3ab3beb4f0e6
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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