Ethyl Acetate → HCID 57686090, compound

HRID 1038081Notes

Reaction equation

HRID 1038081 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4([CH:46]([OH:48])[CH3:47])[CH2:24][CH2:23][N:22]([CH2:25][C:26](=[O:45])[N:27]5[CH2:32][CH2:31][N:30]([C:33]6[CH:38]=[CH:37][C:36]([C:39]7[N:44]=[CH:43][CH:42]=[CH:41][N:40]=7)=[CH:35][CH:34]=6)[CH2:29][CH2:28]5)[CH2:21]4)=[O:19])[CH:15]=3)[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)=[CH:4][CH:3]=1.CCOC(C)=O>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4([CH:46]([OH:48])[CH3:47])[CH2:24][CH2:23][N:22]([CH2:25][C:26](=[O:45])[N:27]5[CH2:32][CH2:31][N:30]([C:33]6[CH:38]=[CH:37][C:36]([C:39]7[N:40]=[CH:41][CH:42]=[CH:43][N:44]=7)=[CH:35][CH:34]=6)[CH2:29][CH2:28]5)[CH2:21]4)=[O:19])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86614439HCID 86614439, compound

Product 1

HCID 57686090HCID 57686090, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Stirred 3-(1-Hydroxy-ethyl)-1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid [3-(4-fluoro-phenyl)-1Trityl-indazol-5-yl]-amide (7N) (65 mg, 0.073 mmol) in 85% TFA (2 ml) at room temperature overnight. Evaporated solvent. Added EtOAc (50 ml) H2O (20 ml) 2M NaOH (3 ml). Separated organic layer, dried over MgSO4, filtered and solvent evaporated yielding a residue which purified on silica gel eluting with 5% v/v MeOH:EtOAc yielding two diastereomeric racemates.

Workup

  1. dry with materialSeparated organic layer, dried over MgSO4
  2. filtrationfiltered
  3. customsolvent evaporated
  4. customyielding a residue which
  5. custompurified on silica gel eluting with 5% v/v MeOH

Sources & evidence

ORD record
ord-e7e0e023d565413db215e22b2b7fece9
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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