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Triethylamine → (R)-tert-butyl 4-(1-(4-(trifluoromethyl)phenylsulfonamido)ethyl)benzoate

HRID 1049082
Notes
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Reaction equation

HRID 1049082 reaction equation
Cl.[C:2]([O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([C@H:14]([NH2:16])[CH3:15])=[CH:10][CH:9]=1)([CH3:5])([CH3:4])[CH3:3].[F:18][C:19]([F:31])([F:30])[C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C)C=O>[F:31][C:19]([F:18])([F:30])[C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:16][C@@H:14]([C:11]2[CH:10]=[CH:9][C:8]([C:7]([O:6][C:2]([CH3:3])([CH3:5])[CH3:4])=[O:17])=[CH:13][CH:12]=2)[CH3:15])(=[O:28])=[O:27])=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 67395949tert-butyl-4-[(1R)-1-aminoethyl]benzoate hydrochloride

Product 1

HCID 67395467(R)-tert-butyl 4-(1-(4-(trifluoromethyl)phenylsulfonamido)ethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a vial containing tert-butyl-4-[(1R)-1-aminoethyl]benzoate hydrochloride from Step 1 was added N,N-dimethylaminopyridine (3.91 mg, 0.032 mmol), 4-(trifluoromethyl)benzenesulfonyl chloride (0.059 g, 0.24 mmol), N,N-dimethylformamide (2 mL), and triethylamine (0.18 mL, 1.28 mmol). The mixture was stirred at rt for 16 h, after which the solvent was fully evaporated. To the residue was added 1,2-dichloroethane (3 mL), sat. NaHCO3 solution (0.5 mL), and water (0.5 mL). After separation, the aqueous layer was extracted with 1,2-dichloroethane (2×3 mL). The combined organic phases were evaporated to dryness to give (R)-tert-butyl 4-(1-(4-(trifluoromethyl)phenylsulfonamido)ethyl)benzoate as a brown solid. LC-MS: (FA) ES+ 430.

Workup

  1. customafter which the solvent was fully evaporated
  2. additionTo the residue was added 1,2-dichloroethane (3 mL), sat. NaHCO3 solution (0.5 mL), and water (0.5 mL)
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with 1,2-dichloroethane (2×3 mL)
  5. customThe combined organic phases were evaporated to dryness

Sources & evidence

ORD record
ord-a33739f3d5dd4ca7b218cdb369eb9d9b
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09382197B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes