Sodium Hydroxide → HCID 178520644、化合物

HRID 491880ノート

反応式

HRID 491880 の反応式
[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

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 576783284-Formyl-5-nitro-2-phenoxypyridineHCID 178511821HCID 178511821、化合物

生成物 1

HCID 178520644HCID 178520644、化合物

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c3f07be6b11b4af092fbf1fba882bcca
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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