Water → HCID 69720467, compound

HRID 263675Notes

Reaction equation

HRID 263675 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][C@H:13]([C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)[C@H:14]([N:16]([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)[C:17]([C@@H:19]([OH:28])[C@@H:20]([C:25]([OH:27])=[O:26])[CH2:21][C:22]([O-:24])=[O:23])=[O:18])[CH3:15].[Na+].[Na+].O1[C:55]2C=CC=[CH:59][C:54]=2N=C1/C=C/C[C@H](C1C=CC2OCOC=2C=1)[C@H](N(CC1C=CC2C(=CC=CC=2)C=1)C([C@@H](O)[C@@H](C(O)=O)CC([O-])=O)=O)C.C(Br)C=C.O>CN(C)C=O>[CH2:59]([O:26][C:25]([C:20](=[C:19]([C:17](=[O:18])[N:16]([C@H:14]([CH3:15])[C@@H:13]([C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)[CH2:12]/[CH:11]=[CH:10]/[C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=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)[OH:28])[CH2:21][C:22]([OH:24])=[O:23])=[O:27])[CH:54]=[CH2:55]

Participants

5

Reactant 3

HCID 962WaterHCID 7841Allyl bromide2×HCID 86751031HCID 86751031, compound

Product 1

HCID 69720467HCID 69720467, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

69 mg of disodium (3S,4S)-4-[N-{(1R,2R,4E)-5-(2-benzoxazolyl)-1-methyl-2-(3,4-methylenedioxyphenyl)-4-pentenyl}-N-(2-naphthylmethyl)carbamoyl]-3-carboxy-4-hydroxybutanoate obtained in Example 67, was dissolved in 3 ml of dimethylformamide, and 19 μl of allyl bromide was added thereto, followed by stirring for 6 hours. Then, 19 μl of allyl bromide was additionally added, followed by further stirring for 15 hours. The reaction solution was poured into water, 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). The obtained diallyl ester was treated in the same manner as in Example 69(2) and (3) to obtain 17 mg (yield: 25%) of the above-identified compound as colorless oily substance.

Workup

  1. stirringby further stirring for 15 hours
  2. extractionextracted with ethyl ether
  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 silica gel column chromatography (hexane/ethyl acetate=3/2)
  7. additionThe obtained diallyl ester was treated in the same manner as in Example 69(2) and (3)

Sources & evidence

ORD record
ord-43586a38d38e443db1cb81b54f9aa330
Source dataset
uspto-grants-1997_07
Patent number
US05643958

Reaction notes

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