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

HRID 2186660

反応式

HRID 2186660 の反応式
[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]

参加物

5

反応物 3

HCID 111,2-Dichloroethane2 回HCID 10513992(1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanolHCID 184596133,6-Dioxadodecanoic acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-43d287bbab694ecbb21f02c503f11f47
出典データセット
uspto-grants-2002_06
特許番号
US06407064B2

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