Sodium Hydroxide → HCID 178520644, 화합물

HRID 491880노트

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HRID 491880 반응식
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([C:28](=[O:39])[CH2:29][CH2:30][C@H:31]([NH2:38])[CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH2:18][CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:40]([C:43]1[C:44]([CH:56]=O)=[CH:45][C:46]([O:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[N:47][CH:48]=1)([O-:42])=[O:41].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl.CCOC(C)=O>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([CH2:18][CH2:19][O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:28](=[O:39])[CH2:29][CH2:30][C@H:31]([NH:38][CH2:56][C:44]2[C:43]([N+:40]([O-:42])=[O:41])=[CH:48][N:47]=[C:46]([O:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH:45]=2)[CH:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 576783284-Formyl-5-nitro-2-phenoxypyridineHCID 178511821HCID 178511821, 화합물

생성물 1

HCID 178520644HCID 178520644, 화합물

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-[[4-amino-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-(2-benzyloxy-ethyl)-amino]-cis-cyclohexanecarboxylic acid benzyl ester (1.9 g, 3.5 mmol) and 5-nitro-2-phenoxy-pyridine-4-carboxaldehyde (0.86 g, 3.53 mmol) in 1,2 dichloroethane (100 mL) was stirred at room temperature for 4 hours, and then NaBH(OAc)3 (1.4 g, 6.6 mmol) was added. The resulting mixture was stirred at room temperature overnight. Then 1N NaOH was added, and the reaction mixture was then poured into EtOAc (200 mL). The organic layer washed with aq. NaCl, dried with MgSO4, filtered, and evaporated to yield a residue. The residue was purified by column chromatography (1:1 heptane/EtOAc) to yield 4-{(2-benzyloxy-ethyl)-[4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-amino}-cis-cyclohexanecarboxylic acid benzyl ester as an oil.

후처리

  1. washThe organic layer washed with aq. NaCl
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a residue
  6. customThe residue was purified by column chromatography (1:1 heptane/EtOAc)

출처 및 근거

ORD 기록
ord-c3f07be6b11b4af092fbf1fba882bcca
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531545B2

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