Sodium Hydroxide → HCID 69215949, compound

HRID 279274Notes

Reaction equation

HRID 279274 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[CH2:8][N:9]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15](=[O:38])[CH2:16][NH:17][C:18](=[O:37])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=2[NH:29]C(OC(C)(C)C)=O)[CH2:10]1)(=[O:3])[CH3:2].[OH-].[Na+]>Cl.O1CCOCC1>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[CH2:8][N:9]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15](=[O:38])[CH2:16][NH:17][C:18](=[O:37])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:22]=[CH:21][C:20]=2[NH2:29])[CH2:10]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69215566HCID 69215566, compound

Product 1

HCID 69215949HCID 69215949, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The resulting (R)-1-(3-acetylamino-4-methoxybenzyl)-3-[{N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine was dissolved in 50% 6 N hydrochloric acid in dioxane and the solution was stirred at room temperature for 2 h. The mixture was adjusted to pH 10 with 5 M NaOH solution, and extracted with ethyl acetate. The organic layer was evaporated and preparative TLC (SiO2, AcOEt/MeOH=4:1) afforded (R)-1-(3-acetylamino-4-methoxybenzyl)-3-[{N-(2-amino-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine (Compound No. 2152) (3.7 mg, 8%): The purity was determined by RPLC/MS (100%); ESI/MS m/e 508.3 (M++H, C24H28F3N5O4).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-71a564df44954acc8f1021e586b940ef
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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