Sodium Hydroxide → HCID 53921056, compound

HRID 1743504Notes

Reaction equation

HRID 1743504 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-96a5c04373d4468b82a560c35557bca7
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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