Trifluoroacetic acid → HCID 89573222, compound

HRID 74830Notes

Reaction equation

HRID 74830 reaction equation
C(OC([NH:8][C@H:9]([C:36]([O:38][CH3:39])=[O:37])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:35])[CH2:19][NH:20][C:21](=[O:34])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]2[C:31](=[O:32])[CH:30]=[CH:29][C:28]2=[O:33])=[CH:13][CH:12]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[O:33]=[C:28]1[CH:29]=[CH:30][C:31](=[O:32])[N:27]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C:21]([NH:20][CH2:19][C:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C@@H:9]([C:36]([O:38][CH3:39])=[O:37])[NH2:8])=[CH:12][CH:13]=1)=[O:35])=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89573429methyl N-(tert-butoxycarbonyl)-4-({N-[6-(2,5-dioxo-2,5-dihydro-1H pyrrol-1-yl)hexanoyl]glycyl}amino)-L-phenylalaninate

Product 1

HCID 89573222HCID 89573222, compoundYield 122.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of #251 (800 mg, 1.47 mmol, 1 eq.) in dichloromethane (16 mL) was added TFA (4.8 mL) at 0° C. The mixture was stirred at room temperature for 2 hours. The mixture was concentrated in vacuo. The residue was dissolved in water and filtered. The filtrate was lyophilized to afford #252 (800 mg, 97.5%) as a white solid. HPLC (Protocol Q3) [M+H+] 1445.4, retention time=0.90 min.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-232dbea785644fd3850729a05f0d5bd8
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

Loading…