Trifluoroacetic acid → HCID 131721464, compound

HRID 1604006Notes

Reaction equation

HRID 1604006 reaction equation
[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:19])[N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[O:9][C:8]([C:20]([O:22]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:21])=[CH:7][C@@H:6]1[NH:36][CH2:37]C(=O)C(F)(F)F)(=[O:3])[CH3:2].[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]>ClCCl>[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47].[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:19])[N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[O:9][C:8]([C:20]([OH:22])=[O:21])=[CH:7][C@@H:6]1[NH:36][CH3:37])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131721465HCID 131721465, compound

Product 1

HCID 131721464HCID 131721464, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of (4S,5R,6R)-5-acetylamino-6-(dipropylcarbamoyl)-4-(2,2,2-trifluoroacetylmethylamino)-5,6-dihydro-4H-pyran-2-carboxylic acid, benzhydryl ester (0.430 g) in dichloromethane (2.5 ml) and trifluoroacetic acid (2.5 ml) was stirred at 23° C. for 2 hours. The solvent was removed in vacuo and the residue was azeotroped with toluene (2×25 ml). The residue was taken up in a water/methanol mixture (20 ml, 1:1 v/v) and stirred at 23° C. with potassium carbonate (1.0 g) for 18 hours. The solvent was removed in vacuo and the residue was purified using HPLC on a reverse phase column eluted in a gradient procedure with water and acetonitrile containing trifluoroacetic acid. The required fractions were combined and solvent was removed in vacuo to give the title compound as a white solid (0.182 g). 1H NMR (250 MHz, D6 -DMSO,) 9.00 (2H, broad s), 8.35 (1H, d, J=8 Hz), 5.92 (1H, d, J=3 Hz), 5.05 (1H, d, J=8 Hz), 4.34 (1H, m), 3.46-3.30 (2H, m), 3.25-3.10 (1H, m), 3.08-2.90 (1H, m), 2.6 (3H, s), 1.75 (3H, s), 1.60-1.48 (2H, m), 1.48-1.30 (2H, m), 0.80 (3H, t, J=8 Hz), 0.75 (3H, t, J=8 Hz). Mass spec (Low Resolution): MH+ =342. Mass spec (High Resolution): MH+ =342.202998, fits for molecular formula C16H28N3O5, error=0.3 ppm.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was azeotroped with toluene (2×25 ml)
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified
  5. washeluted in a gradient procedure with water and acetonitrile
  6. additioncontaining trifluoroacetic acid
  7. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-25ca699b0fd947c7a969a15d3ce84698
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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