Triethylamine → tert-Butyl 3-((3,5-dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate

HRID 1889621Notes

Reaction equation

HRID 1889621 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[CH:30]=[CH:29][C:10]([CH2:11][NH:12][CH2:13][C:14]3[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=3)[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Cl:33][C:34]1[C:35]([OH:45])=[C:36]([S:41](Cl)(=[O:43])=[O:42])[CH:37]=[C:38]([Cl:40])[CH:39]=1.CCN(CC)CC>C(Cl)Cl>[Cl:33][C:34]1[C:35]([OH:45])=[C:36]([S:41]([N:12]([CH2:13][C:14]2[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=2)[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:11][C:10]2[CH:29]=[CH:30][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:32][CH:31]=3)=[CH:8][CH:9]=2)(=[O:43])=[O:42])[CH:37]=[C:38]([Cl:40])[CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 66616559tert-Butyl 3-((4-(4-fluorophenoxy)benzylamino)methyl)benzylcarbamate

Product 1

HCID 58531654tert-Butyl 3-((3,5-dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamateYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 3-((4-(4-fluorophenoxy)benzylamino)methyl)benzylcarbamate (0.72 g, 1.64 mmol) in CH2Cl2 (15 mL) added 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride (0.45 g, 1.72 mmol) and Et3N (0.68 ml, 4.91 mmol). The reaction mixture was stirred at 0° C. under nitrogen for 1.5 h. The reaction mixture was concentrated and the residue was extracted with ethyl acetate and saturated NaHCO3 solution. The organic layer was washed successively with brine, 1 N HCl, brine, and concentrated after drying over MgSO4 to give viscous solid (0.99 g, 82%). 1H NMR (CDCl3): δ 9.10 (bs, 1H), 7.52 (d, J=2.8 Hz, 1H), 7.40 (d, J=2.8 Hz, 1H), 7.28-7.17 (m, 1H), 7.14-6.90 (m, 9H), 6.85 (d, J=8.3 Hz, 2H), 4.36 (m, 4H), 4.23 (m, 2H), 1.46 (s, 9H); MS (ESI): (M+H)+=605.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate and saturated NaHCO3 solution
  3. washThe organic layer was washed successively with brine, 1 N HCl, brine
  4. concentrationconcentrated
  5. dry with materialafter drying over MgSO4

Sources & evidence

ORD record
ord-a7926490de73409c81b78cd61aff0a60
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

Loading…