Sodium Trifluoroacetate → HCID 13341010, compound

HRID 1262571Notes

Reaction equation

HRID 1262571 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:12]([NH:14][CH2:15][CH2:16][C@H:17]([OH:21])[C:18](O)=[O:19])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C([O-])=O.[Na+]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:12]([N:14]1[CH2:15][CH2:16][C@H:17]([OH:21])[C:18]1=[O:19])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517019Sodium TrifluoroacetateHCID 13341007HCID 13341007, compound

Product 1

HCID 13341010HCID 13341010, compound

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Procedure

6.5 g of (S)-4-[(3-benzyloxy-4-methoxybenzoyl)amino]-2-hydroxybutyric acid and 1.0 g of sodium trifluoroacetate are boiled at reflux while stirring in 40 ml of trifluoroacetic acid anhydride for 48 hours. After evaporation of the mixture, the residue is shaken three times with toluene, and the toluene is thereafter evaporated in vacuo. The residue, containing (S)-1-(3-benzyloxy-4-methoxybenzoyl)-2-oxo-3-pyrrolidinyltrifluoroacetate, is boiled at reflux in 40 ml of absolute methanol for 30 minutes. Thereafter, the mixture is stirred at room temperature for an additional 1 hour, whereupon the solid material is removed by filtration and washed with methanol. There is obtained (S)-1-(3-benzyloxy-4-methoxybenzoyl)-3-hydroxy-2-pyrrolidinone which melts at 166°-167° after recrystallization from methanol; [α]D20 =-146°; [α]54620 =-180°; [α]36520 =-879° (chloroform, c=1.0).

Workup

  1. temperatureat reflux
  2. customAfter evaporation of the mixture
  3. customthe toluene is thereafter evaporated in vacuo
  4. additionThe residue, containing (S)-1-(3-benzyloxy-4-methoxybenzoyl)-2-oxo-3-pyrrolidinyltrifluoroacetate
  5. temperatureat reflux in 40 ml of absolute methanol for 30 minutes
  6. stirringThereafter, the mixture is stirred at room temperature for an additional 1 hour, whereupon the solid material
  7. customis removed by filtration
  8. washwashed with methanol

Sources & evidence

ORD record
ord-be7ec939d3e04c87a6db99c4d559fef7
Source dataset
uspto-grants-1984_06
Patent number
US04452807

Reaction notes

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