4-Toluenesulfonyl chloride → HCID 88192779, compound

HRID 2185441Notes

Reaction equation

HRID 2185441 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.[CH2:12]1[C:20]2[C:15](=[CH:16][C:17]([NH:21][C:22](=[O:36])[C@@H:23]3[CH2:27][C@H:26]([OH:28])[CH2:25][N:24]3[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:12]1[C:20]2[C:15](=[CH:16][C:17]([NH:21][C:22](=[O:36])[C@@H:23]3[CH2:27][C@H:26]([O:28][S:7]([C:4]4[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=4)(=[O:9])=[O:8])[CH2:25][N:24]3[C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chloride2×HCID 70173032HCID 70173032, compound

Product 1

HCID 88192779HCID 88192779, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

4-Dimethylaminopyridine (4.1 g) and p-toluenesulphonyl chloride (4.8 g) were added to a solution of cis-4-hydroxy-N-tert-butoxycarbonyl-L-proline 5-indanylamide (B, 5.8 g) in dichloromethane (85 mL) at 0° C. After stirring at room temperature for 6 hr, additional 4-dimethylaminopyridine (1.0 g) and p-toluenesulphonyl chloride (1.6 g) were added. The resulting solution was stirred at room temperature for 19 hr, and the solvent was evaporated in vacuo. The residue was diluted with ethyl acetate, and washed with 0.5 M citric acid, saturated sodium hydrogen carbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo to afford the title compound (7.4 g) as a pale brown sticky oil: 1H NMR (400 MHz, CD3OD) δ 1.3-1.6 (m, 9H), 2.10 (m, 2H), 2.2 (m, 1H), 2.39 (s, 3H), 2.5 (m, 1H), 2.88 (m, 4H), 3.68 (m, 2H), 4.3-4.4 (m, 1H), 5.17 (m, 1H), 7.15 (m, 2H), 7.31-7.35 (m, 3H), and 7.73 (d, J=7.8 Hz, 2H).

Workup

  1. stirringThe resulting solution was stirred at room temperature for 19 hr
  2. customthe solvent was evaporated in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with 0.5 M citric acid, saturated sodium hydrogen carbonate, and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f39eb55cedeb42c59aebda9acd9ff8f2
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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