Hydrochloric Acid → HCID 9939870, compound

HRID 263670Notes

Reaction equation

HRID 263670 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][CH:13]([C:49]1[CH:54]=[CH:53][C:52]2[O:55][CH2:56][O:57][C:51]=2[CH:50]=1)[CH:14]([N:16]([CH2:38][C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=1)[C:17]([CH2:19][CH:20]([C:33]([O:35]CC)=[O:34])[CH:21]([C:28]([O:30]CC)=[O:29])[CH2:22][C:23]([O:25]CC)=[O:24])=[O:18])[CH3:15].[OH-].[Na+].Cl>O1CCCC1.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][CH:13]([C:49]1[CH:54]=[CH:53][C:52]2[O:55][CH2:56][O:57][C:51]=2[CH:50]=1)[CH:14]([N:16]([CH2:38][C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=1)[C:17]([CH2:19][CH:20]([C:33]([OH:35])=[O:34])[CH:21]([C:28]([OH:30])=[O:29])[CH2:22][C:23]([OH:25])=[O:24])=[O:18])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18705272HCID 18705272, compound

Product 1

HCID 9939870HCID 9939870, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The N-acylated compound obtained in the above step (1) was treated in the same manner as in Example 27 to obtain triethyl 4-[N-{(1RS,2RS,4E)-5-(2-benzoxazolyl)-1-methyl-2-(3,4-methylenedioxyphenyl)-4-pentenyl}-N-(2-naphthylmethyl)carbamoyl]-1,2,3-butanetricarboxylate. The obtained ester was dissolved in 1 ml of tetrahydrofuran, and then 0.5 ml of a 3N sodium hydroxide aqueous solution was added thereto. The mixture was left to stand at room temperature overnight. The reaction solution was diluted with ethyl acetate and then acidified by an addition of 1N hydrochloric acid, and it was washed with a saturated sodium chloride aqueous solution and then 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 A, RP-8, manufactured by Merck Co.; acetonitrile/0.1% trifluoroacetic acid aqueous solution=1/1) to obtain 14 mg (yield: 52%) of the above-identified compound as white powder.

Workup

  1. waitThe mixture was left
  2. washwas washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by medium pressure liquid chromatography (Lobar column™, size A, RP-8, manufactured by Merck Co.; acetonitrile/0.1% trifluoroacetic acid aqueous solution=1/1)

Sources & evidence

ORD record
ord-1e09cab2511d42099a3240b6ecf190cf
Source dataset
uspto-grants-1997_07
Patent number
US05643958

Reaction notes

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