Triethylamine → (2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]-1-(3-pyridylmethyl)pyrrolidine

HRID 654166ノート

反応式

HRID 654166 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:16][NH:15][C@H:14](/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Cl)[CH:28]=1.C(N(CC)CC)C>O1CCCC1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C@H:12]2[CH2:16][N:15]([CH2:33][C:29]3[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=3)[C@H:14](/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:13]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 15670385(2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine

生成物 1

HCID 15670386(2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]-1-(3-pyridylmethyl)pyrrolidine収率 56.7%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of (2S, 4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine (1.00 g), 3-picolylchloride hydrochloride (509 mg) and triethylamine (0.43 ml) in tetrahydrofuran (25 ml) was refluxed for 48 hours and the solution was diluted with chloroform (40 ml). The solution was washed successively with saturated aqueous sodium bicarbonate and brine, and the organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel (50 g) column with a mixture of chloroform and methanol (100:1) as an eluent to give (2S, 4R)-4-(4-chlorophenylsulfonylamino)-2[(Z)-5-methoxycarbonyl-1-pentenyl]-1-(3-pyridylmethyl)pyrrolidine (700 mg) as a pale brown oil.

後処理

  1. temperaturewas refluxed for 48 hours
  2. washThe solution was washed successively with saturated aqueous sodium bicarbonate and brine
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was chromatographed on a silica gel (50 g) column with a mixture of chloroform and methanol (100:1) as an eluent

出典と根拠

ORDレコード
ord-72f728ccfd82462ab1569a709f8d0c55
出典データセット
uspto-grants-1992_07
特許番号
US05130323

反応ノート

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