Trifluoroacetic acid → methyl (9R,11S,14S)-14-tert-butyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.1 9,12]octacosa-1(26),2(28),3,5,22,24-hexaene-11-carboxylate

HRID 1879260Notes

Reaction equation

HRID 1879260 reaction equation
[C:1]([C@@H:5]1[NH:29][CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=[CH:23][C:22]2[CH:30]=[C:18]([CH:19]=[CH:20][CH:21]=2)[C:17]2=[CH:31][C:13](=[CH:14][CH:15]=[CH:16]2)[CH2:12][O:11][C@H:10]2[CH2:32][N:7]([C@H:8]([C:33]([O:35][CH3:36])=[O:34])[CH2:9]2)[C:6]1=[O:37])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>CO.[Pd]>[C:1]([C@@H:5]1[NH:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][C:22]2[CH:30]=[C:18]([CH:19]=[CH:20][CH:21]=2)[C:17]2=[CH:31][C:13](=[CH:14][CH:15]=[CH:16]2)[CH2:12][O:11][C@H:10]2[CH2:32][N:7]([C@H:8]([C:33]([O:35][CH3:36])=[O:34])[CH2:9]2)[C:6]1=[O:37])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58005114Methyl (9R,11S,14S,20E)-14-tert-butyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.1 9,12]octacosa-1(26),2(28),3,5,20,22,24-heptaene-11-carboxylate

Product 1

HCID 58005141methyl (9R,11S,14S)-14-tert-butyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.1 9,12]octacosa-1(26),2(28),3,5,22,24-hexaene-11-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C 10% (20% w/w) was added to a 0.025 M solution of methyl (9R,11S,14S,20E)-14-tert-butyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.1 9,12]octacosa-1(26),2(28),3,5,20,22,24-heptaene-11-carboxylate 103 in MeOH containing trifluoroacetic acid (1.0 eq.). The reaction mixture was stirred under a hydrogen atmosphere for 6 h. Solids were filtered off and the resulting solution was evaporated under reduced pressure. The residue was used without further purification in the following step. MS (ES+) m/z 507 (M+H)+.

Workup

  1. filtrationSolids were filtered off
  2. customthe resulting solution was evaporated under reduced pressure
  3. customThe residue was used without further purification in the following step

Sources & evidence

ORD record
ord-ef6f50d790304b10b61887ef20733604
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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