4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-[tert-butoxycarbonyl-(3-fluoro-benzyl)-amino]-ethyl ester

HRID 8639

Reaction equation

HRID 8639 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][C:13]([O:16][C:17](=[O:30])[N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[CH2:19][CH2:20][OH:21])([CH3:15])[CH3:14].FC1C=C(C=CC=1)CNCCO.C(N(CC)CC)C>ClCCl>[C:13]([O:16][C:17]([N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[CH2:19][CH2:20][O:21][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])=[O:30])([CH3:12])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 108667492-(3-Fluoro-benzylamino)-ethanolHCID 69653122tert-butyl N-[(3-fluorophenyl)methyl]-N-(2-hydroxyethyl)carbamate

Product 1

HCID 23548235Toluene-4-sulfonic acid 2-[tert-butoxycarbonyl-(3-fluoro-benzyl)-amino]-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add p-toluenesulfonyl-chloride (0.71 g, 3.71 mmol), portionwise, to a mixture of (3-fluoro-benzyl)-(2-hydroxy-ethyl)-carbamic acid dimethyl-ethyl ester (1 g, 3.71 mmol, prepared from 2-(3-fluoro-benzylamino)-ethanol by methods as are known in the art), triethylamine (0.751 g, 7.4 mmol) and dichloromethane (6 mL). Stir the resulting suspension vigorously overnight at room temperature. Add water (10 mL), separate the organic layer, and extract the aqueous layer with dichloromethane (5 mL), twice. Combine the organic layers and wash with citric acid (5 mL, 20% in water), dry with sodium sulfate and evaporate the solvent to give the final, desired compound. The final compound may be purified by chromatography.

Workup

  1. customAdd water (10 mL), separate the organic layer
  2. extractionextract the aqueous layer with dichloromethane (5 mL)
  3. washwash with citric acid (5 mL, 20% in water)
  4. dry with materialdry with sodium sulfate
  5. customevaporate the solvent

Sources & evidence

ORD record
ord-3bfb9478b47f4e919a8a0e2f00a8190d
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Linked notes

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