Hydrochloric Acid → Diisopropylethylamine

HRID 993210노트

반응식

HRID 993210 반응식
C=[C:2]1[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([N:20]([C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:21][CH2:22][CH3:23])[CH2:16][CH2:15]2)[CH2:3]1.Cl.CC[O:37][CH2:38][CH3:39].[CH3:40]O>>[CH3:22][CH2:21][N:20]([CH:38]([CH3:39])[CH3:40])[CH:17]([CH3:18])[CH3:16].[CH2:27]([NH:26][C:24]([N:20]([CH:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH:4]2[CH:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:6][C:2](=[O:37])[CH2:3]2)[CH2:15][CH2:16]1)[CH2:21][CH2:22][CH3:23])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3283Diethyl EtherHCID 701578021-Methylene-3-(SR)-((4-(N-(benzylaminocarbonyl)-N-(prop-1-yl)amino)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentane

생성물 2

HCID 81531Diisopropylethylamine수율 1%HCID 701580783-(SR)-((4-(N-(Benzylaminocarbonyl)-N-(prop-1-yl)amino)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentan-1-one

실험 절차

To a solution of 1-methylene-3-(SR)-((4-(N-(benzylaminocarbonyl)-N-(prop-1-yl)amino)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentane from Step D (1.8 g, 4.0 mmol) in methanol (50 mL) was added 1M hydrogen chloride in ether (6.0 mL, 6.0 mmol). The solution was cooled in a dry ice/acetone bath and ozone was bubbled into the solution until the blue color persisted. The excess ozone was removed with a stream of nitrogen and then dimethylsulfide (5 mL) was added. After 10 min, the bath was removed and the reaction was allowed to warm to rt over 16 h. The volatiles were removed in vacuo and the residue was purified by FC (ethyl acetate, then 1% DIPEA in ethyl acetate) to give the title compound (1.13 g).

후처리

  1. temperatureThe solution was cooled in a dry ice/acetone bath
  2. customozone was bubbled into the solution until the blue color
  3. customThe excess ozone was removed with a stream of nitrogen
  4. additiondimethylsulfide (5 mL) was added
  5. customthe bath was removed
  6. customThe volatiles were removed in vacuo
  7. customthe residue was purified by FC (ethyl acetate

출처 및 근거

ORD 기록
ord-7ee420401b6f40e196434632229fc3c2
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472410B1

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