Trifluoroacetic acid → HCID 131720770, compound

HRID 1956739Notes

Reaction equation

HRID 1956739 reaction equation
C([N:8]([CH2:39][CH3:40])[CH2:9][C:10]([NH:12][C@H:13]([C:25]([NH:27][C@H:28]([C:36]([NH2:38])=[O:37])[CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:26])[CH2:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:11])(OC(C)(C)C)=O.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>ClCCl>[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42].[NH:8]([CH2:39][CH3:40])[CH2:9][C:10]([NH:12][C@H:13]([C:25]([NH:27][C@H:28]([C:36]([NH2:38])=[O:37])[CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:26])[CH2:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12991453HCID 12991453, compound

Product 1

HCID 131720770HCID 131720770, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

BOC-N(Et)Gly-(L)-Asp(OBzl)-(L)-Cha-NH2 is dissolved in dichloromethane (~1:12 wt/wt), and to that solution is added TFA at ambient temperature. This is then stirred until HPLC indicates complete reaction (3-5 hours). The solution is concentrated to about 1/2 volume at 40°-45° C. To this warm solution is added MTBE (~1:10 wt/wt vs. BOC-N(Et)Gly-(L)-Asp(OBzl)-(L)-Cha-NH2) while maintaining the temperature >40° C. The mixture is slowly cooled to about 5° C. and stirred for 1 hour to ensure complete crystallization. The resulting solids are filtered, and washed with chilled MTBE. The solids are dried under reduced pressure and analyzed for content of TFA·N(Et)Gly-(L)-Asp(OBzl)-(L)-Cha-NH2 (HPLC wt/wt assay). Yield is generally nearly quantitative, purity >95 A %.

Workup

  1. customreaction (3-5 hours)
  2. concentrationThe solution is concentrated to about 1/2 volume at 40°-45° C
  3. additionTo this warm solution is added MTBE (~1:10 wt/wt vs. BOC-N(Et)Gly-(L)-Asp(OBzl)-(L)-Cha-NH2)
  4. temperaturewhile maintaining the temperature >40° C
  5. stirringstirred for 1 hour
  6. customcrystallization
  7. filtrationThe resulting solids are filtered
  8. washwashed with chilled MTBE
  9. customThe solids are dried under reduced pressure
  10. customYield

Sources & evidence

ORD record
ord-9ab17e96c5c2401cae94cf58eca17c4c
Source dataset
uspto-grants-1998_07
Patent number
US05780590

Reaction notes

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