Trifluoroacetic acid → (3R,10S)-2-methyl-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid

HRID 965139Notes

Reaction equation

HRID 965139 reaction equation
C([O:5][C:6](=[O:37])[CH:7]([CH3:36])[C@H:8]([C:13](=[O:35])[NH:14][C@H:15]1[CH2:32][C:31]2=[CH:33][N:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=32)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[O:34])[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.C(O)(C(F)(F)F)=O>ClCl>[CH3:36][CH:7]([C@H:8]([C:13](=[O:35])[NH:14][C@H:15]1[CH2:32][C:31]2=[CH:33][N:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=32)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[O:34])[CH2:9][CH:10]([CH3:11])[CH3:12])[C:6]([OH:37])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70092174(3R,10S)-2-methyl-5-methyl-3-(9-oxo-1,8-diazatricyclo-[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid t-butyl ester

Product 1

HCID 67693784(3R,10S)-2-methyl-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

Alternatively, the less polar stereoisomer of (3R,10S)-2-methyl-5-methyl-3-(9-oxo-1,8-diazatricyclo-[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid t-butyl ester prepared in Example 5D above (15 mg) was taken up in CH2 Cl2 (2.4 mL) and TFA (0.6 mL) and the resulting mixture was stirred at room temperature for 4 hrs. The solvent was removed under reduced pressure at 35° C. Then ethyl acetate was added and the solution was washed with water (3×10 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Recrystallization from ethyl acetate/petroleum ether gave (3R,10S)-2-methyl-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid as a white solid (7 mg), MS: 456.3 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure at 35° C
  2. additionThen ethyl acetate was added
  3. washthe solution was washed with water (3×10 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customRecrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-92a6c391d4474233bd754f59fc726e19
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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