(3R,10S)-5-methyl-3-(9-oxo-1,8-diaza-tricyclo-[10.6.1.013,18]nonadeca-12(19), 13(18), 14,16-tetraen-10-ylcarbamoyl)hexanoic acid t-butyl ester → 5-Methyl-3-(9-oxo-1,8-diaza-tricyclo(10.6.1.013,18)nonadeca-12(19),13,15,17-tetraen-10-ylcarbamoyl)-hexanoic acid

HRID 849722Notes

Reaction equation

HRID 849722 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][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]([CH3:12])[CH3:11])(C)(C)C>C(O)(C(F)(F)F)=O>[CH3:11][CH:10]([CH3:12])[CH2:9][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])[CH2:7][C:6]([OH:36])=[O:5]

Participants

3

Reactant 1

HCID 70094604(3R,10S)-5-methyl-3-(9-oxo-1,8-diaza-tricyclo-[10.6.1.013,18]nonadeca-12(19), 13(18), 14,16-tetraen-10-ylcarbamoyl)hexanoic acid t-butyl ester

Product 1

HCID 52893145-Methyl-3-(9-oxo-1,8-diaza-tricyclo(10.6.1.013,18)nonadeca-12(19),13,15,17-tetraen-10-ylcarbamoyl)-hexanoic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Alternatively, (3R,10S)-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 (3.24 g, 6.5 mmol) was taken up in 95% TFA (aqueous) (30 mL) at 0° C. and then stirred for 20 minutes. The ice bath was then removed and the mixture was stirred for another 1 hour. After concentrating it to an oil, the residue was taken up in ethyl acetate (250 mL) and washed with water (7×150 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness to yield a single stereoisomer of (3R,10S)-5-methyl-3-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid as a white powder, 2.83 g (98.4% yield); MS: 442 (M+H)+

Workup

  1. customThe ice bath was then removed
  2. stirringthe mixture was stirred for another 1 hour
  3. concentrationAfter concentrating it to an oil
  4. washwashed with water (7×150 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-cf8b0d8eb83f4ec2ac97444272b09d80
Source dataset
uspto-grants-2000_01
Patent number
US06013792

Reaction notes

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