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Tris(1,1-dimethylethyl)phosphine → Benzyl 6-(3-(phenylsulfonyl)quinolin-8-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

HRID 2068133
ノート
印刷プレビュー

反応式

HRID 2068133 の反応式
CC(C)([O-])C.[Na+].[C@@H:7]12[CH2:13][NH:12][C@@H:11]1[CH2:10][N:9]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:8]2.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.I[C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:47]=1[N:46]=[CH:45][C:44]([S:48]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=[O:50])=[O:49])=[CH:43]2>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:51]1([S:48]([C:44]2[CH:45]=[N:46][C:47]3[C:42]([CH:43]=2)=[CH:41][CH:40]=[CH:39][C:38]=3[N:12]2[CH2:13][CH:7]3[CH:11]2[CH2:10][N:9]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:8]3)(=[O:50])=[O:49])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 114067748-Iodo-3-(phenylsulfonyl)quinolineHCID 23635906benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylateHCID 23676156Sodium t-butoxide

生成物 1

HCID 25196270Benzyl 6-(3-(phenylsulfonyl)quinolin-8-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

A solution of sodium t-butoxide (49 mg, 0.51 mmol) and (1S,5S)-benzyl 3,6-diazabicyclo[3.2.0]heptane-3-carboxylate (98 mg, 0.24 mmol) in toluene (3 mL) was stirred under nitrogen. To this was added tri-t-butylphosphine (25 mg, 0.05 mmol), palladium (II) acetate (6.9 mg, 0.03 mmol) and 8-iodo-3-(phenylsulfonyl)quinoline (80 mg, 0.202 mmol). The mixture was then heated at 60° C. for 2 h before partitioning between CH2Cl2 and water. The mixture was filtered through Celite and the organic phase was separated. The water phase was extracted twice with CH2Cl2 and the combined extracts dried (Na2SO4), filtered and concentrated in vacuo to provide the crude material, which was purified by flash chromatography to give the title compound.

後処理

  1. custombefore partitioning between CH2Cl2 and water
  2. filtrationThe mixture was filtered through Celite
  3. customthe organic phase was separated
  4. extractionThe water phase was extracted twice with CH2Cl2
  5. dry with materialthe combined extracts dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide the crude material, which
  9. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-bcf8ab7bb7294575ab874b7aa9d40c94
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08293913B2

反応ノート

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