Trifluoroacetic acid → Trifluoroacetate

HRID 441190Notes

Reaction equation

HRID 441190 reaction equation
C(OC([CH:8]([C:40]1[N:41]=[CH:42][NH:43][CH:44]=1)[O:9][C:10]([NH:12][C:13]1[C:14](=[O:39])[N:15]([CH2:25][C:26]([NH:28][CH:29]([CH:36]([CH3:38])[CH3:37])[C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[O:27])[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:17][CH:18]=1)=[O:11])=O)(C)(C)C.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>ClCCl>[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[NH:43]1[CH:44]=[C:40]([CH2:8][O:9][C:10]([NH:12][C:13]2[C:14](=[O:39])[N:15]([CH2:25][C:26]([NH:28][CH:29]([CH:36]([CH3:37])[CH3:38])[C:30](=[O:35])[C:31]([F:33])([F:34])[F:32])=[O:27])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[O:11])[N:41]=[CH:42]1.[F:45][C:46]([F:51])([F:50])[C:47]([O-:49])=[O:48]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid3×HCID 178449513HCID 178449513, compound

Product 2

HCID 84468TrifluoroacetateHCID 178449512HCID 178449512, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[3-(1-tert-butoxycarbonylimidazol-4-ylmethoxycarbonylamino)-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.134 g) in dry dichloromethane was added trifluoroacetic acid (0.018 mL). After stirring for 1 h, the reaction was not complete; so additional trifluoracetic acid (0.018 mL) was added. Following 17 h more stirring, the reaction was still incomplete. Additional trifluoroacetic acid (0.036 mL) was added and the reaction mixture was stirred 6 h (complete deprotection), evaporated and dried under high vacuum to give the title compound as a trifluoroacetate salt; TLC: Rf =O.10, dichloromethane:methanol (94:6); MS: 520(M+1).

Workup

  1. waitFollowing 17 h
  2. stirringmore stirring
  3. stirringthe reaction mixture was stirred 6 h (complete deprotection)
  4. customevaporated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-37ca8d33a145499bac6c14d77f0142c8
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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