HCID 69213603, compound → HCID 44453366, compound

HRID 1280968Notes

Reaction equation

HRID 1280968 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[OH:39])[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:35])[CH2:13][NH:14][C:15](=[O:34])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[NH:26]C(OC(C)(C)C)=O)[CH2:7]1>Cl.O1CCOCC1>[NH2:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[OH:39])[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:35])[CH2:13][NH:14][C:15](=[O:34])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:19]=[CH:18][C:17]=2[NH2:26])[CH2:7]1

Participants

4

Reactant 1

HCID 69213603HCID 69213603, compound

Product 1

HCID 44453366HCID 44453366, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (R)-1-(3-amino-4-hydroxybenzyl)-3-[{N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine (20 mg), prepared pursuant to methods of Example 808, in 4 N HCl in dioxane (2.0 mL) was stirred at room temperature overnight. After the solution was concentrated, the residue was dissolved in methanol, loaded onto Varian™ SCX column, washed with CH3OH, and eluted off using 2 N NH3 in CH3OH. Concentration and preparative TLC (SiO2, AcOEt/MeOH=4:1) afforded (R)-1-(3-amino-4-hydroxybenzyl)3-[{N-(2-Amino-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine (Compound No. 2187) (9.6 mg, 59%): The purity was determined by RPLC/MS (86%); ESI/MS m/e 452.3 (M++H, C21H24F3N5O3).

Workup

  1. concentrationAfter the solution was concentrated
  2. dissolutionthe residue was dissolved in methanol
  3. washwashed with CH3OH
  4. washeluted off
  5. concentrationConcentration and preparative TLC (SiO2, AcOEt/MeOH=4:1)

Sources & evidence

ORD record
ord-2611cd5f44f64e97a3a73730e54d0b85
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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