Ammonium Hydroxide → (10S)-2-mercaptomethyl-4-methyl-N-(9-oxo-1,8-diazatricyclo[10.6.1.013,18]-nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide

HRID 965148Notes

Reaction equation

HRID 965148 reaction equation
C([S:4][CH2:5][CH:6]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:7]([NH:9][C@H:10]1[CH2:27][C:26]2=[CH:28][N:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=32)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][NH:12][C:11]1=[O:29])=[O:8])(=O)C.[NH4+].[OH-]>CO>[SH:4][CH2:5][CH:6]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:7]([NH:9][C@H:10]1[CH2:27][C:26]2=[CH:28][N:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=32)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][NH:12][C:11]1=[O:29])=[O:8]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86752869(10S)-2-acetylthiomethyl-4-methyl-N-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide

Product 1

HCID 86752870(10S)-2-mercaptomethyl-4-methyl-N-(9-oxo-1,8-diazatricyclo[10.6.1.013,18]-nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the less polar stereoisomer of (10S)-2-acetylthiomethyl-4-methyl-N-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide (50 mg, 0.106 mmol) in 10 mL of methanol at 0° C. under argon was added 0.5 mL concentrated NH4OH. The reaction mixture was stirred from 0° C. (ice-bath was removed after addition of NH4OH) to room temperature and further stored at room temperature for 1 hour. Excess methanol was removed under reduced pressure to give a white solid residue. The residue was partitioned between ethyl acetate (30 mL) and 0.1 NHCl (15 mL). The organic layer was washed with brine (15 mL), dried (MgSO4), and evaporated to dryness. The solid residue was stirred in 50% ether/pet. ether and filtered to yield the more polar stereoisomer of (10S)-2-mercaptomethyl-4-methyl-N-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-yl)pentanamide as a white powder, 41 mg (90%) m.p. 224° C.

Workup

  1. custom(ice-bath was removed after addition of NH4OH) to room temperature
  2. customExcess methanol was removed under reduced pressure
  3. customto give a white solid residue
  4. customThe residue was partitioned between ethyl acetate (30 mL) and 0.1 NHCl (15 mL)
  5. washThe organic layer was washed with brine (15 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. stirringThe solid residue was stirred in 50% ether/pet. ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-0a75e6649715444a9b7594e3b8fa4f3b
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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