Hydrochloric Acid → HCID 70128860, compound

HRID 1004328Notes

Reaction equation

HRID 1004328 reaction equation
[C:1]([O:5][C:6]([C:8](=[C:14]([C:16](=[O:52])[N:17]([CH:27]([CH3:51])[CH:28]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:29][C:30]1[O:31][C:32]([C:35](=[O:43])[NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:33][CH:34]=1)[CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:15])[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]([C:16](=[O:52])[N:17]([CH:27]([CH3:51])[CH:28]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:29][C:30]1[O:31][C:32]([C:35](=[O:43])[NH:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:33][CH:34]=1)[CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:15])[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70296054HCID 70296054, compound

Product 1

HCID 70128860HCID 70128860, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

68 mg of methyl 3-(tert-butoxycarbonyl)-4-[N-[(1RS,2RS)-2-(tert-butoxycarbonyl)-1-methyl-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-{(E)-3-phenyl-2-propenyl}carbamoyl]-4-hydroxy-3-butenoate was dissolved in a mixture of 3 ml of tetrahydrofuran and 1 ml of water and stirred together with 1 ml of 1N aqueous sodium hydroxide at room temperature for 40 hours. The reaction solution was acidified with 1N hydrochloric acid and 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=20/1→10/1] to give 44 mg (yield: 66%) of the title compound as a pale yellow solid.

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=20/1→10/1]

Sources & evidence

ORD record
ord-6f10afaa965d4c3287b8799e6a5592b5
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

Loading…