Lithium Hydroxide → (3R,10S)-2-carboxy-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 849726Notes

Reaction equation

HRID 849726 reaction equation
C[O:2][C:3]([CH:5]([C@H:9]([C:14](=[O:36])[NH:15][C@H:16]1[CH2:33][C:32]2=[CH:34][N:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=32)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:17]1=[O:35])[CH2:10][CH:11]([CH3:13])[CH3:12])[C:6]([OH:8])=[O:7])=[O:4].[Li+].[OH-]>C(O)C>[C:3]([CH:5]([C@H:9]([C:14](=[O:36])[NH:15][C@H:16]1[CH2:33][C:32]2=[CH:34][N:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=32)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:17]1=[O:35])[CH2:10][CH:11]([CH3:13])[CH3:12])[C:6]([OH:8])=[O:7])([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54385960HCID 54385960, compound

Product 1

HCID 15428413(3R,10S)-2-carboxy-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 702EthanolSolvent

Procedure

(3R,10S)-2-Methoxycarbonyl-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 was taken up in ethanol (25 mL) and then 1 N LiOH (0.3 mL, 3 eq) was added dropwise. The resulting homogeneous solution was stirred at room temperature for 3 hrs. Most of the ethanol was removed under reduced pressure at 30° C. Then water (5 mL) and ethyl acetate (30 mL) was added and with stirring, 4 N HCl was added until pH=2. The ethyl acetate layer was further washed with brine, dried over Na2SO4, filtered and evaporated to dryness. Purified by reverse phase HPLC to give 47 mg of (3R,10S)-2-carboxy-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, MS: 484.5 (M-H)-.

Workup

  1. customMost of the ethanol was removed under reduced pressure at 30° C
  2. additionThen water (5 mL) and ethyl acetate (30 mL) was added
  3. stirringwith stirring
  4. addition4 N HCl was added until pH=2
  5. washThe ethyl acetate layer was further washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customPurified by reverse phase HPLC

Sources & evidence

ORD record
ord-230dea664b724f19a1e4383d8452f235
Source dataset
uspto-grants-2000_01
Patent number
US06013792

Reaction notes

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