1,2-Dichloroethane → (1S,2S)-2-(3,6-dioxadodecanoyl)amino-3-morpholino-1-phenyl-1-propanol

HRID 2186660

반응식

HRID 2186660 반응식
[C:1]([OH:14])(=O)[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(Cl)CCl.[NH2:19][C@@H:20]([CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[C@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[OH:22]>C(Cl)Cl>[C:1]([NH:19][C@@H:20]([CH2:29][N:30]1[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1)[C@H:21]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[OH:22])(=[O:14])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

참가 물질

5

반응물 3

HCID 111,2-Dichloroethane2회HCID 10513992(1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanolHCID 184596133,6-Dioxadodecanoic acid

생성물 1

HCID 69821443(1S,2S)-2-(3,6-dioxadodecanoyl)amino-3-morpholino-1-phenyl-1-propanol수율 47.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Methylene chloride (40 ml), 3,6-dioxadodecanoic acid (1.086 g, 5.325 mmol) and EDC (1.167 g, 6.090 mmol) were added to (1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanol (959.1 mg, 4.064 mmol), followed by stirring for 3 hours. EDC (719.3 mg, 3.752 mmol) was added thereto and the mixture was further stirred for 3 days. After evaporating the solvent under reduced pressure, a saturated sodium hydrogen carbonate solution (70 ml) was added, followed by extraction with ethyl acetate (100 ml). After washed with water (70 ml) and saturated brine (70 ml) successively, the organic layer was dried over sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform:methanol=30:1) to obtain the title compound (812.3 mg, yield 47.4%) as colorless oil.

후처리

  1. stirringthe mixture was further stirred for 3 days
  2. customAfter evaporating the solvent under reduced pressure
  3. additiona saturated sodium hydrogen carbonate solution (70 ml) was added
  4. extractionfollowed by extraction with ethyl acetate (100 ml)
  5. washAfter washed with water (70 ml) and saturated brine (70 ml) successively
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe resulting crude product was purified by silica gel column chromatography (chloroform:methanol=30:1)

출처 및 근거

ORD 기록
ord-43d287bbab694ecbb21f02c503f11f47
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06407064B2

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