Sodium Hydroxide → HCID 69215949, compound

HRID 133569Notes

Reaction equation

HRID 133569 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+]>O1CCOCC1.Cl>[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 a 50% dioxane solution of 6 M hydrochloric acid, and the obtained solution was stirred at room temperature for 2 hours, adjusted to pH 10 with a 5 M NaOH solution and extracted with ethyl acetate. The organic layer was concentrated and purified by preparative TLC (SiO2) to thereby provide (R)-1-(3-acetylamino-4-methoxybenzyl)-3-[[N-(2-amino-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine (Compd. 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. concentrationThe organic layer was concentrated
  3. custompurified by preparative TLC (SiO2) to thereby provide (R)-1-(3-acetylamino-4-methoxybenzyl)-3-[[N-(2-amino-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine (Compd. No

Sources & evidence

ORD record
ord-8b7fdf72b1a4401c9882f903dcd38477
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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