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(4-Amino-5-chloro-2,3-dihydrobenzofuran-7-yl)(1H-imidazol-1-yl)methanone → (+/-)-1,1-Dimethylethyl cis-4-[[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]amino]methyl]-3-hydroxy-1-piperidinecarboxylate

HRID 988122
ノート
印刷プレビュー

反応式

HRID 988122 の反応式
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][C@H:4]1[OH:16].[NH2:17][C:18]1[C:23]2[CH2:24][CH2:25][O:26][C:22]=2[C:21]([C:27](N2C=CN=C2)=[O:28])=[CH:20][C:19]=1[Cl:34]>C(#N)C>[NH2:17][C:18]1[C:23]2[CH2:24][CH2:25][O:26][C:22]=2[C:21]([C:27]([NH:1][CH2:2][C@H:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:5][C@H:4]2[OH:16])=[O:28])=[CH:20][C:19]=1[Cl:34]
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

4

反応物 2

HCID 22662740(4-Amino-5-chloro-2,3-dihydrobenzofuran-7-yl)(1H-imidazol-1-yl)methanoneHCID 57983247Tert-butyl (3s,4r)-4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate

生成物 1

HCID 131724101(+/-)-1,1-Dimethylethyl cis-4-[[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]amino]methyl]-3-hydroxy-1-piperidinecarboxylate収率 78%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

A mixture of intermediate (1-f) (0.09 mol) and intermediate (3-c) (0.087 mol) in ACN (600 ml) was stirred and refluxed for 1 hour. The reaction mixture was cooled to 0° C., and the solvent was evaporated. The residue was partitioned between DCM and water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 97/3). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from ACN. The precipitate was filtered off and dried), yielding 28.7 g (78%) of (±)-1,1-dimethylethyl cis-4-[[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]amino]methyl]-3-hydroxy-1-piperidinecarboxylate (interm. 4. mp. 218° C.).

後処理

  1. temperaturerefluxed for 1 hour
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between DCM and water
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 97/3)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from ACN
  12. filtrationThe precipitate was filtered off
  13. customdried),

出典と根拠

ORDレコード
ord-4d6e5ddb45fd4cde94ff6b00b3ec3b93
出典データセット
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06635643B2

反応ノート

読み込み中…

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