Water → HCID 19364484, compound

HRID 581035Notes

Reaction equation

HRID 581035 reaction equation
[CH3:1][CH:2]([NH:28][CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)[CH:3]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[CH2:4][C:5]1[O:6][C:7]([C:10](=[O:18])[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:9]=1.C([O:43][CH:44]([C:60]([O-])=[O:61])[CH:45]([C:54]([O:56][CH:57]([CH3:59])[CH3:58])=[O:55])[CH2:46][CH2:47][C:48]([O:50][CH:51]([CH3:53])[CH3:52])=[O:49])(=O)C.CC(C)[O-].[Na+].O>C(O)(C)C>[OH:43][CH:44]([C:60](=[O:61])[N:28]([CH:2]([CH3:1])[CH:3]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[CH2:4][C:5]1[O:6][C:7]([C:10](=[O:18])[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:9]=1)[CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)[CH:45]([C:54]([O:56][CH:57]([CH3:59])[CH3:58])=[O:55])[CH2:46][CH2:47][C:48]([O:50][CH:51]([CH3:53])[CH3:52])=[O:49]

Participants

6

Reactant 4

HCID 962WaterHCID 109204432-Propanol, sodium salt (1:1)HCID 19364487HCID 19364487, compoundHCID 131721295HCID 131721295, compound

Product 1

HCID 19364484HCID 19364484, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

99 mg of isopropyl 5-acetoxy-4-isopropoxycarbonyl-5-[N-[(1RS,2RS)-1-methyl-2-(4-nitrophenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-(2-naphthylmethyl)carbamoyl]pentanoate obtained by subjecting N-{(1RS,2RS)-1-methyl-2-(4-nitrophenyl)3-{5-(phenylcarbamoyl)-2-furyl}propyl]-2-naphthylmethylamine obtained in Example 23(1) and 2,4-diisopropyl 1-acetoxy-1,2,4-butanetricarboxylate obtained in Reference Example 5 to a condensation reaction in accordance with the method of Example 24(1), was dissolved in 3 ml of isopropanol, and 9.8 mg of sodium isopropoxide was added thereto, followed by stirring at room temperature for one hour. The reaction solution was poured into water and extracted with ethyl acetate. Then, 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 silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain 43 mg (yield: 45%) of the above-identified compound.

Workup

  1. customobtained in Reference Example 5 to a condensation reaction in accordance with the method of Example 24(1)
  2. extractionextracted with ethyl acetate
  3. dry with materialThen, the organic layer was dried 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 silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-77241b67300f48dd8da403a311e5b406
Source dataset
uspto-grants-1999_07
Patent number
US05919786

Reaction notes

Loading…