Ammonium Chloride → HCID 178508038、化合物

HRID 491881ノート

反応式

HRID 491881 の反応式
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([CH2:47][CH2:48][O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:18](=[O:46])[CH2:19][CH2:20][C@H:21]([NH:28][CH2:29][C:30]2[C:35]([N+:36]([O-])=O)=[CH:34][N:33]=[C:32]([O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:31]=2)[CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>CO.[Zn]>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:12][CH2:13][C@@H:14]([N:17]([C:18](=[O:46])[CH2:19][CH2:20][C@H:21]([NH:28][CH2:29][C:30]2[C:35]([NH2:36])=[CH:34][N:33]=[C:32]([O:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:31]=2)[CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH2:47][CH2:48][O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 178520644HCID 178520644、化合物

生成物 1

HCID 178508038HCID 178508038、化合物

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

Zinc dust (21.4 g, 330 mmol) was carefully added into a solution of 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 (1.85 g, 2.4 mmol) and NH4Cl (2.6 g, 48 mmol) in MeOH (300 mL). The resulting mixture was refluxed 4 hours. The MeOH was removed before EtOAc (300 mL) was added. The resulting solution washed with aq. NaHCO3 and aq. NaCl. The organic layer was dried with MgSO4, filtered, and evaporated to yield 4-[[4-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-(2-benzyloxy-ethyl)-amino]-cis-cyclohexanecarboxylic acid benzyl ester as a light brown oil.

後処理

  1. temperatureThe resulting mixture was refluxed 4 hours
  2. customThe MeOH was removed before EtOAc (300 mL)
  3. additionwas added
  4. washThe resulting solution washed with aq. NaHCO3 and aq. NaCl
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-9d2cf31b9e9a463ebce8e9329f2febef
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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