Ethyl Acetate → HCID 44453405, compound

HRID 1280963Notes

Reaction equation

HRID 1280963 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([N+:24]([O-])=O)[CH:18]=2)[CH2:12]1)=[O:9])=[O:5].C(OCC)(=O)C>[Pd].CO>[NH2:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[Cl:23])[CH2:16][N:13]1[CH2:14][CH2:15][C@@H:11]([NH:10][C:8](=[O:9])[CH2:7][NH:6][C:4](=[O:5])[C:3]2[CH:27]=[C:28]([C:31]([F:34])([F:32])[F:33])[CH:29]=[CH:30][C:2]=2[NH2:1])[CH2:12]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 53714627HCID 53714627, compound

Product 1

HCID 44453405HCID 44453405, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-3-[{N-(2-amino-5-trifluoromethylbenzoyl)glycyl}amino]-1-(4-chloro-3-nitrobenzyl)pyrrolidine (32.6 mg), 10% Pd-activated carbone (8 mg), ethyl acetate (2.7 mL) and methanol (0.3 mL) was stirred under a hydrogen atmosphere at room temperature for 15 h. The Pd catalyst was filtered off, and the filtrate was concentrated. Solid phase extraction (Bond Elut™ SI, 20% methanol/AcOEt) afforded (R)-1-(3-amino-4-chlorobenzyl)-3-[{N-(2-amino-5-trifluoromethylbenzoyl)glycyl}amino]pyrrolidine (Compound No. 2132) (10.5 mg, 34%): The purity was determined by RPLC/MS (84%); ESI/MS m/e 470.2 (M++H, C21H23ClF3N5O2).

Workup

  1. filtrationThe Pd catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. extractionSolid phase extraction (Bond Elut™ SI, 20% methanol/AcOEt)

Sources & evidence

ORD record
ord-22f82c95d1d04b048683a247639b5dfb
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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