Water → HCID 69721146, compound

HRID 581034Notes

Reaction equation

HRID 581034 reaction equation
[CH3:1][CH:2]([N:28]([CH2:41][C:42]1[CH:51]=[CH:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=1)[C:29]([CH:31]([OH:40])[CH:32]([C:37]([O-:39])=[O:38])[CH2:33][C:34]([O-:36])=[O:35])=[O:30])[CH:3]([C:19]1[CH:24]=[CH:23][C:22]2[O:25][CH2:26][O:27][C:21]=2[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.[Na+].[Na+].O[C:55]([C:65](=O)N(C(C)C(C1C=CC2OCOC=2C=1)CC1OC(C(=O)NC2C=CC=CC=2)=CC=1)CC1C=CC2C(=CC=CC=2)C=1)=[C:56](C(OC)=O)CC(O)=O.C(Br)C=C.O>CN(C)C=O>[CH2:65]([O:38][C:37]([C:32](=[C:31]([OH:40])[C:29](=[O:30])[N:28]([CH:2]([CH3:1])[CH:3]([C:19]1[CH:24]=[CH:23][C:22]2[O:25][CH2:26][O:27][C:21]=2[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)[CH2:41][C:42]1[CH:51]=[CH:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=1)[CH2:33][C:34]([OH:36])=[O:35])=[O:39])[CH:55]=[CH2:56]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 70300683HCID 70300683, compoundHCID 86753438HCID 86753438, compound

Product 1

HCID 69721146HCID 69721146, compoundYield 2.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80 mg of disodium (3RS,4RS)-4-[N-[(1RS,2RS)-1-methyl-2-(3,4-methylenedioxyphenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-(2-naphthylmethyl)carbamoyl]-3-carboxylato-4-hydroxybutanoate as the starting material of Example 28, was dissolved in 2 ml of dimethylformamide, and 37 μl of allyl bromide was added thereto, followed by stirring at room temperature for 3 days. The reaction solution was poured into water and extracted with ethyl ether 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 silica gel column chromatography (hexane/ethyl acetate=3/2), and the obtained diallyl ester was treated in the same manner as in Example 25(2) and (3) to obtain 4.4 mg (yield: 2.4%) of the above-identified compound as a colorless oily substance.

Workup

  1. extractionextracted with ethyl ether
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2)
  6. additionthe obtained diallyl ester was treated in the same manner as in Example 25(2) and (3)

Sources & evidence

ORD record
ord-b5d1174651c04ecbbf5aeff9eafdbf0f
Source dataset
uspto-grants-1999_07
Patent number
US05919786

Reaction notes

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