Hydrochloric Acid → HCID 9939870, compound

HRID 2287490Notes

Reaction equation

HRID 2287490 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.C(#N)C>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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 18705272HCID 18705272, compound

Product 1

HCID 9939870HCID 9939870, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The N-acylated product obtained in (1) was converted to triethyl 4-[N-{(1RS,2RS,4E)-5-(2-benzoxazolyl)-1-methyl-2-(3,4-methylendioxyphenyl)-4-pentenyl}-N-(2-naphthylmethyl)carbamoyl]-1,2,3-butanetricarboxylate in the same manner as in Preparation Example 1. The resulting ester was dissolved in 1 ml of tetrahydrofuran, and after addition of 0.5 ml of 3N sodium hydroxide, it was left standing at room temperature overnight. The reaction solution was diluted with ethyl acetate, acidified with 1N hydrochloric acid, washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was evaporated in vacuo. The residue was purified by medium pressure liquid chromatography [Lobar column™, size A, RP-8 (Merck & Co., Inc.); acetonitrile/0.1% aqueous trifluoroacetic acid=1/1] to give 14 mg (yield 52%) of the title compound as a white powder.

Workup

  1. waitwas left
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by medium pressure liquid chromatography [Lobar column™, size A

Sources & evidence

ORD record
ord-f7d31a6cbd644deb83c046301b44eb82
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Reaction notes

Loading…