Sodium Hydroxide → 4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide

HRID 491873ノート

反応式

HRID 491873 の反応式
[NH2:1][CH:2]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:3][CH2:4][C:5]([N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:8][CH2:9][OH:10])=[O:6].[N+:23]([C:26]1[C:27]([CH:39]=O)=[CH:28][C:29]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:30][CH:31]=1)([O-:25])=[O:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl>[CH:17]1([CH:2]([NH:1][CH2:39][C:27]2[C:26]([N+:23]([O-:25])=[O:24])=[CH:31][N:30]=[C:29]([O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:28]=2)[CH2:3][CH2:4][C:5]([N:7]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:8][CH2:9][OH:10])=[O:6])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 576783284-Formyl-5-nitro-2-phenoxypyridineHCID 670234664-amino-4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-butyramide

生成物 1

HCID 670236094,N-dicyclohexyl-N-(2-hydroxy-ethyl)-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of 4-amino-4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-butyramide (2.0 g, 6.5 mmol) and 5-nitro-2-phenoxypyridine-4-carbaldehyde (1.6 g, 6.5 mmol) in 1,2 dichloroethane (50 mL), NaBH(OAc)3 (2.0 g, 9.4 mmol) was added, and the reaction mixture was stirred at room temperature overnight. After the addition of 1N NaOH solution, the reaction mixture was then extracted with EtOAc (200 mL×2). The organic layer was dried with Mg2SO4 and then evaporated to a residue which was purified by column chromatography to yield 4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide as an oil.

後処理

  1. extractionthe reaction mixture was then extracted with EtOAc (200 mL×2)
  2. dry with materialThe organic layer was dried with Mg2SO4
  3. customevaporated to a residue which
  4. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-587f9a63548a4741bf5ef7ec41704ff9
出典データセット
uspto-grants-2009_05
特許番号
US07531545B2

反応ノート

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