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 849724Notes

Reaction equation

HRID 849724 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>C(Cl)Cl>[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 6344DichloromethaneSolvent

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 CH2Cl2 (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-f39ecf09af6144df946725d4dfa9ae82
Source dataset
uspto-grants-2000_01
Patent number
US06013792

Reaction notes

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