Trifluoroacetic acid → HCID 22644767, compound

HRID 2414636Notes

Reaction equation

HRID 2414636 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][S:18][C:17]([CH3:22])([CH3:21])[CH:16]2[C:23]([O-:25])=[O:24])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][S:18][C:17]([CH3:21])([CH3:22])[CH:16]2[C:23]([OH:25])=[O:24])(=[O:13])=[O:14])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22644864HCID 22644864, compound

Product 1

HCID 22644767HCID 22644767, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-({[4-(2-butynyloxy)phenyl]sulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylate (0.31 g, 0.71 mmol) in dichloromethane (7 mL) was added trifluoroacetic acid (3 mL) and the resulting mixture was stirred at room temperature for 1 hour, after which the solvents were evaporated and toluene was added. The toluene and excess trifloroacetic acid were removed to give 0.25 g of (3S)-4-({[4-(2-butynyloxy)phenyl]sulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid, which was used for the next step without further purification. Yield: 92.6%. mp 129-131° C. %. Electrospray Mass Spec 381.8(M−H)−.

Workup

  1. customafter which the solvents were evaporated
  2. additiontoluene was added
  3. customThe toluene and excess trifloroacetic acid were removed

Sources & evidence

ORD record
ord-7390e4a29ab04f9484f58bcfcfd2b65d
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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