Dichloromethane → HCID 89525943, compound

HRID 920270Notes

Reaction equation

HRID 920270 reaction equation
[Br:1][C:2]1[C:3]([S:31](=[O:50])(=[O:49])[N:32](CC2C=CC(OC)=CC=2OC)[C:33]2[S:37][N:36]=[CH:35][N:34]=2)=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([C@@H:11]([C:13]3[CH:14]=[CH:15][CH:16]=[C:17]4[C:22]=3[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)[CH3:12])[C:6]=2[CH:30]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O>CO>[Br:1][C:2]1[C:3]([S:31]([NH:32][C:33]2[S:37][N:36]=[CH:35][N:34]=2)(=[O:50])=[O:49])=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([C@@H:11]([C:13]3[CH:14]=[CH:15][CH:16]=[C:17]4[C:22]=3[CH2:21][NH:20][CH2:19][CH2:18]4)[CH3:12])[C:6]=2[CH:30]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 117638131HCID 117638131, compound

Product 1

HCID 89525943HCID 89525943, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Added 35-4 (120 mg, 0.153 mmol) to DCM (610 μl) and TFA (306 μl). After 90 min, diluted with 1 mL MeOH, filtered through Celite, washed with MeOH. Concentrated filtrate in vacuo and dissolved in 2 mL DMSO. Purified by reverse-phase HPLC (C18 column, 2-60% 0.1% TFA/CH3CN:0.1% TFA/H2O) to give 35-5 as a white solid

Workup

  1. filtrationfiltered through Celite
  2. washwashed with MeOH
  3. dissolutionConcentrated filtrate in vacuo and dissolved in 2 mL DMSO
  4. customPurified by reverse-phase HPLC (C18 column, 2-60% 0.1% TFA/CH3CN:0.1% TFA/H2O)

Sources & evidence

ORD record
ord-295f1705754c4b1a8b9932a33d399a90
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

Loading…