Tris(hydroxymethyl)aminomethane → HCID 87239817, compound

HRID 2198062Notes

Reaction equation

HRID 2198062 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C@@H:16]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:15][CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH2:25][C:26]([CH2:31][OH:32])([CH2:29][OH:30])[CH2:27][OH:28]>CO.O>[NH2:25][C:26]([CH2:31][OH:32])([CH2:29][OH:30])[CH2:27][OH:28].[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C@@H:16]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:15][CH2:14]2)[CH:4]=[C:3]([C:2]([F:24])([F:1])[F:23])[CH:8]=1

Participants

5

Reactant 2

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 44538650HCID 44538650, compound

Product 1

HCID 87239817HCID 87239817, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-{(2R,5S)-5-[3,5-bis(trifluoromethyl)phenyl]tetrahydrofuran-2-yl}propanoic acid (3.00 g, 8.42 mmol) obtained in Example 36 in methanol (60 mL) was added a solution of tromethamine (1.02 g, 8.42 mmol) in water (5 mL), and the mixture was stirred at room temperature for 2 hr. The solution was concentrated under reduced pressure, and the obtained solid was dissolved in ethyl acetate/toluene (10:1, 50 mL), and concentrated under reduced pressure. The obtained solid was disrupted in diisopropyl ether to give the title compound (3.79 g, yield 94%) as a white solid. Mp 110° C. Anal. Calcd. for C19H25NO6F6: C, 47.80; H, 5.28; N, 2.93. Found: C, 47.61; H, 5.47; N, 2.99.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe obtained solid was dissolved in ethyl acetate/toluene (10:1, 50 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e01c0be2cee14be6b7a519d3b6505d91
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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