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

HRID 491873노트

반응식

HRID 491873 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-587f9a63548a4741bf5ef7ec41704ff9
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531545B2

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