Triethylamine → HCID 58531386, compound

HRID 1889625Notes

Reaction equation

HRID 1889625 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][NH:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:23]=2)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:4][CH:3]=1.[Cl:34][C:35]1[C:36]([OH:46])=[C:37]([S:42](Cl)(=[O:44])=[O:43])[CH:38]=[C:39]([Cl:41])[CH:40]=1.CCN(CC)CC>C1COCC1>[Cl:34][C:35]1[C:36]([OH:46])=[C:37]([S:42]([N:7]([CH2:8][C:9]2[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:23]=2)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:33][CH:32]=2)(=[O:44])=[O:43])[CH:38]=[C:39]([Cl:41])[CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 58531569HCID 58531569, compound

Product 1

HCID 58531386HCID 58531386, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-((4-fluorobenzylamino)methyl)-5-(4-fluorophenoxy)benzylcarbamate (0.72 g, 1.58 mmol) in THF (15 mL) were added 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (0.41 g, 1.58 mmol) and Et3N (0.66 mL, 4.75 mmol). The reaction mixture was stirred at rt for 1.5 h. The mixture was concentrated. The sample was purified by flash chromatography. Elution with 0 to 35% of ethyl acetate in dichloromethane gave the product as a white solid (0.65 g, 61%). 1H NMR (CDCl3): δ 9.01 (s, 1H), 7.55 (d, J=2.0 Hz, 1H), 7.45 (s, 1H), 7.15-7.06 (m, 4H), 7.01-6.92 (m, 4H), 6.76 (s, 2H), 6.54 (s, 1H), 4.41 (s, 2H), 4.32 (s, 2H), 4.21 (d, J=5.6 Hz, 2H), 1.49 (s, 9H); MS (ESI): (M−H)−=677.1.

Workup

  1. concentrationThe mixture was concentrated
  2. customThe sample was purified by flash chromatography
  3. washElution with 0 to 35% of ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-69acb502267b49a4bb5f54ad2a0e44ba
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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