HCID 10472407, compound → HCID 10464987, compound

HRID 1708585Notes

Reaction equation

HRID 1708585 reaction equation
[O:1]=[C:2]1[C:6]([CH2:7][C@H:8]([NH:16]C(OC(C)(C)C)=O)[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:5][C:4](=[O:24])[NH:3]1>C(C(O)=O)(F)(F)F>[O:1]=[C:2]1[C:6]([CH2:7][C@H:8]([NH2:16])[C:9]([OH:11])=[O:10])=[CH:5][C:4](=[O:24])[NH:3]1

Participants

3

Reactant 1

HCID 10472407HCID 10472407, compound

Product 1

HCID 10464987HCID 10464987, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 11 (0.4 g, 1.17 mmol) was dissolved in CF3CO2H and the mixture was stirred at room temperature overnight. The excess CF3CO2H was evaporated under vacuum and the resulting residue was chromatographed on a cationexchange column (AG 50W-X8) with water as the eluting solvent. The fractions containing the product were lyophilized to give 0.18 g (83%) of 2 as a white solid: mp 142° C. dec; [α]D +5° (c 0.5, H2O); 1H NMR (300 MHz, D2O) δ 3.1-3.2 (m, 2 H, CH2), 4.42-4.48 (m, 1 H, α-CH), 6.76 (s, 1 H, HC=C); 13C NMR (75 MHz, D2O) δ 26.02 (CH2), 52.31 (α-C), 130.87 (C=CH), 144.01 (C=CH), 171.89 (C--O), 173.07 (C=O), 173.53 (C=O). Anal. (C7H8N2O4) C, H, N.

Workup

  1. customThe excess CF3CO2H was evaporated under vacuum
  2. customthe resulting residue was chromatographed on a cationexchange column (AG 50W-X8) with water as the eluting solvent
  3. additionThe fractions containing the product

Sources & evidence

ORD record
ord-843eb3710fba4097b9f3309eea6edf81
Source dataset
uspto-grants-1994_10
Patent number
US05359087

Reaction notes

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