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Triethylamine → Propyl (7R)-7-[[(4-fluorophenyl)sulfonyl]amino]-6,7,8,9-tetrahydropyrido[1,2-a]indole-10-acetate

HRID 475489
ノート
印刷プレビュー

反応式

HRID 475489 の反応式
[NH2:1][C@H:2]1[CH2:21][N:6]2[C:7]3[C:12]([C:13]([CH2:14][C:15]([O:17][CH2:18][CH2:19][CH3:20])=[O:16])=[C:5]2[CH2:4][CH2:3]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:1][C@H:2]2[CH2:21][N:6]3[C:7]4[C:12]([C:13]([CH2:14][C:15]([O:17][CH2:18][CH2:19][CH3:20])=[O:16])=[C:5]3[CH2:4][CH2:3]2)=[CH:11][CH:10]=[CH:9][CH:8]=4)(=[O:31])=[O:30])=[CH:25][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 58349691(R)-propyl 2-(7-amino-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

生成物 1

HCID 58399163Propyl (7R)-7-[[(4-fluorophenyl)sulfonyl]amino]-6,7,8,9-tetrahydropyrido[1,2-a]indole-10-acetate収率 97%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒

実験手順

To a CH2Cl2 solution (0.2 M) of propyl ([7R]-7-amino-6,7,8,9-tetrahydro-pyrido[1,2-α]indo1-10-yl)acetate from Step 6 was added 4-fluorobenzenesulfonyl chloride (1.1 equiv.) followed by triethylamine (3 equiv.) and DMAP (1 equiv.). The reaction mixture was stirred for 12 h at rt. The mixture was concentrated under reduced pressure, diluted with EtOAc, and washed with aqueous NaHCO3, water and finally with brine. The organic layer was dried with Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel using a CombiFlashRF (Teledyne ISCO) eluting with EtOAc/Hex (10:90 to 50:50) to give the title compound (97%) as a colorless foam.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washwashed with aqueous NaHCO3, water and finally with brine
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel using a CombiFlashRF (Teledyne ISCO)
  8. washeluting with EtOAc/Hex (10:90 to 50:50)

出典と根拠

ORDレコード
ord-9eb9697f134b4b07aa6d73718b378104
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637541B2

反応ノート

読み込み中…

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