Trifluoroacetic acid → HCID 57905070, compound

HRID 1093055Notes

Reaction equation

HRID 1093055 reaction equation
C(OC(=O)C([N:12]1[CH2:19][CH:18]2[CH2:20][CH:14]([C:15]3[N:16]([C:21](=[O:31])[C:22]([OH:30])=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:24]=3)[CH2:17]2)[CH2:13]1)=CC(OCC)=O)C.FC(F)(F)C(O)=O>C(#N)C>[OH:30][C:22]1[C:21](=[O:31])[N:16]2[CH2:17][CH:18]3[CH2:20][CH:14]([C:15]2=[N:24][C:23]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:13][NH:12][CH2:19]3

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66588808HCID 66588808, compound

Product 1

HCID 57905070HCID 57905070, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

To diethyl-2-(2-(ethoxycarbonyl)-3-hydroxy-4-oxo-7,8,10,11-tetrahydro-4H-7,11-methanopyrimido[1,2-a][1,5]diazocin-9(6H)-yl)-2-butenedioate (0.300 g, 0.673 mmol) in acetonitrile (15 mL) was added trifluoroacetic acid (1 mL) at 23° C. The reaction mixture was stirred at 23° C. for 6 hours. CH3CN and trifluoroacetic acid were then removed in vacuo and the crude material was redissolved in toluene and dried again (2×30 mL) to afford 234 mg (90% yield) of the title trifluoroacetic salt. LCMS (+ESI, M+H+) m/z: 280.

Workup

  1. customCH3CN and trifluoroacetic acid were then removed in vacuo
  2. dissolutionthe crude material was redissolved in toluene
  3. customdried again (2×30 mL)
  4. customto afford 234 mg (90% yield) of the title trifluoroacetic salt

Sources & evidence

ORD record
ord-80c22ff101f84d9d975250af038e5b1c
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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