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 965148노트

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HRID 965148 반응식
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]

참가 물질

4

반응물 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

생성물 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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0a75e6649715444a9b7594e3b8fa4f3b
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773428

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