2-Propenoic acid, 2,5-dioxo-1-pyrrolidinyl ester → HCID 22880304, compound

HRID 399546Notes

Reaction equation

HRID 399546 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][CH2:6][CH2:7][C:8]([C@@H:10]([C@H:12]([C@H:18]([C@@H:20]([CH2:22][OH:23])[OH:21])[OH:19])[O:13][CH2:14][C:15]([OH:17])=[O:16])[OH:11])=[O:9].[C:24](ON1C(=O)CCC1=O)(=[O:27])[CH:25]=[CH2:26]>O.CO.C(N(CC)CC)C>[C:24]([NH:1][CH2:2][CH2:3][S:4][CH2:5][CH2:6][CH2:7][C:8]([C@@H:10]([C@H:12]([C@H:18]([C@@H:20]([CH2:22][OH:23])[OH:21])[OH:19])[O:13][CH2:14][C:15]([OH:17])=[O:16])[OH:11])=[O:9])(=[O:27])[CH:25]=[CH2:26]

Participants

5

Reactant 2

HCID 1815082-Propenoic acid, 2,5-dioxo-1-pyrrolidinyl esterHCID 86753224HCID 86753224, compound2×

Product 1

HCID 22880304HCID 22880304, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Compound 9 (1.5 g) was dissolved in water/methanol (1:1, 10 mL) to which triethylamine was added to obtain pH 10. N-acryloyloxy succinimide (2.0 g) was added and the mixture was stirred for 2 hr. After TLC analysis indicated the complete disappearance of starting material 9, the volatiles were removed from the reaction mixture. The residue was chromatographed on a silica gel column using 20% methanol in dichloromethane. The appropriate fractions were pooled and solvent was removed to give the derivative 10 as a white foam (1.1g). 1H NMR (D2O) : δ, 1.62-1.95, mm, 6H; 2.64-2.80, m, 2H; 3.05-3.14, m, 2H; 3.28-3.35, m, 1H; 3.68-3.72, dd, 1H; 4.11-4.15, m, 2H; 4.24-4.29, m, 1H; 4.38-4.41, m, 2H; 5.82-5.86,dd, 2H, acryloyl CH2; 6.26-6.36,m, 1H, acryloyl CH: 13C NMR (D2O): 176.92, 175.14, 168.12, 129.42, 78.76, 74.44, 71.47, 66.38, 66.41, 65.70, 60.72, 38.21, 30.11, 27.62, 24.49, 22.31.

Workup

  1. additionwas added
  2. customto obtain pH 10
  3. customthe volatiles were removed from the reaction mixture
  4. customThe residue was chromatographed on a silica gel column
  5. customsolvent was removed

Sources & evidence

ORD record
ord-607cfbe10ec4456f8884ea49331b7caa
Source dataset
uspto-grants-1998_10
Patent number
US05821312

Reaction notes

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