Sodium Hydroxide → HCID 53921056, compound

HRID 1884748Notes

Reaction equation

HRID 1884748 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:31]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]2C=C[CH:45]=[CH:44][CH:43]=2)=[O:32])[CH:5]=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[C:7]=1[O:8][CH2:9][CH2:10][NH:11][C:12]([NH:14]C(=O)C(Cl)(Cl)Cl)=[O:13].[OH-].[Na+]>C(Cl)Cl.CO>[CH2:34]([NH:33][C:31]([C:4]1[CH:5]=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=2)[C:7]([O:8][CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[O:13])=[C:2]([Br:1])[CH:3]=1)=[O:32])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22237643HCID 22237643, compound

Product 1

HCID 53921056HCID 53921056, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 5-bromo-N-(8-phenyloctyl)-6-[2-({[(2,2,2-trichloroacetyl) amino]carbonyl} amino)ethoxy]-3′-(trifluoromethyl)[1,1′-biphenyl]-3-carboxamide in CH2Cl2/MeOH (10/4) (14 mL) was added 1M NaOH (2 mL). The reaction was stirred at rt overnight and concentrated in vacuo. The residue was extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (3 to 5% MeOH:CH2Cl2) to afford the title compound (0.203 g, 92%) as a white solid. mp 122.5-125.1° C. 1H NMR (DMSO-d6) δ 8.58 (bt, 1H); 8.12 (d, 1H); 7.90 (m, 3H); 7.78 (d, 1H); 7.73 (dd, 1H); 6.95 (t, 1H); 5.44 (s, 2H); 3.48 (dd, 2H); 3.24 (dd, 2H); 3.05 (ddd, 2H); 1.48 (dd, 2H); 1.25 (m, 18H); 0.84 (t, 3H); IR (KBr) 3300, 2950, 2820, 1650, 1600, 1550, 1460, 1330, 1180, 1120, 1080, 1030, 900, 805 cm−1; mass spectrum [(+)ESI], m/z 614/616 (M+H)+; Anal. Calcd. for C29H39BrF3N3O3: C, 56.68; H, 6.40; N, 6.84, Found: C, 56.37; H, 6.25; N, 6.49.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe residue was extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (3 to 5% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-01484d2bd6d5442596211d326526701a
Source dataset
uspto-grants-2004_07
Patent number
US06765021B2

Reaction notes

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