Trifluoroacetic acid → Glycine iodopropargyl ester trifluoroacetate

HRID 1656154Notes

Reaction equation

HRID 1656154 reaction equation
[I:1][CH:2]([O:5][C:6](=[O:16])[CH2:7][NH:8]C(OC(C)(C)C)=O)[C:3]#[CH:4].[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20]>ClCCl>[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20].[I:1][CH:2]([O:5][C:6](=[O:16])[CH2:7][NH2:8])[C:3]#[CH:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57210957N-t-butoxycarbonylglycine iodopropargyl ester2×

Product 1

HCID 86747289Glycine iodopropargyl ester trifluoroacetateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-t-Butoxycarbonyl glycine iodopropargyl ester (Compound #1) (4.20 g., 12.39 mmole) was dissolved in anhydrous dichloromethane (20 ml.), cooled to 0° C. with an ice-bath, and treated with 10 ml. of trifluoroacetic acid. The reaction mixture was stirred magnetically at 0° C. for 1 hour and then allowed to warm to ambient temperature. The volatile solvents were removed under reduced pressure leaving a clear syrup which crystallized on standing to a white solid (4.20 g., 96% yield) as the desired trifluoroacetate salt product. m.p. 130°-131° C. 1H-NMR (200 MHz, DMSOd6) δ=3.92, s, 2H; 5.00, s; 2H; s; 9.1, broad m. IR (KBr) 1605, 1670, 1765, 2205, 2640 cm-1.

Workup

  1. additiontreated with 10 ml
  2. temperatureto warm to ambient temperature
  3. customThe volatile solvents were removed under reduced pressure
  4. customleaving a clear syrup which
  5. customcrystallized

Sources & evidence

ORD record
ord-5e4adcb2cf3445cf880c864a1c9f07f1
Source dataset
uspto-grants-1993_10
Patent number
US05252745

Reaction notes

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