Sodium Iodide → N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-tert-butyldimethylsiloxy-2-(3-formamido4-benzyloxyphenyl)ethylamine

HRID 2261416

反応式

HRID 2261416 の反応式
Br[CH2:2][C@H:3]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([NH:18][CH:19]=[O:20])[CH:5]=1.[OH:29][C@H:30]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][NH2:41])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.C(OC(C)C)(=O)C.CS(C)=O>[OH:29][C@H:30]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][NH:41][CH2:2][C@H:3]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:4]2[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:6]([NH:18][CH:19]=[O:20])[CH:5]=2)=[CH:35][CH:34]=1

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 100837532-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethylamineHCID 574610672-bromo-(R)-1-tert-butyldimethylsiloxy-1-(3-formamido-4-benzyloxyphenyl)ethane

生成物 1

HCID 57755062N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-tert-butyldimethylsiloxy-2-(3-formamido4-benzyloxyphenyl)ethylamine収率 100%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 7915Isopropyl Acetate溶媒

反応条件

温度
140 °C

実験手順

Intermediate 4 (5.0 g, 11 mmol), intermediate 2 (3.5 g, 14 mmol), and dimethylsulfoxide (10 mL) were combined in a 100 mL round bottom flask and stirred to form a homogeneous solution. Potassium carbonate (6.0 g, 43 mmol) and sodium iodide (1.7 g, 11 mmol) were added and the reaction mixture was heated to 140° C. The reaction mixture was maintained at 140° C. for 10 min, then cooled to room temperature and diluted with water (24 mL) and isopropyl acetate (28 mL). The reaction was stirred until all solids dissolved and then transferred to a separatory funnel. The organic layer was washed with water (17 mL) followed by acetate buffer (5% v/v acetic acid, 12% w/v sodium acetate trihydrate in water, 18 ml) followed by sodium bicarbonate solution (5% w/v in water, 17 mL) followed by saturated aqueous sodium chloride (17 mL). The organic layer was dried over sodium sulfate and concentrated to afford intermediate 5 as a brown gelatinous solid (7.0 g, 11 mmol, >99%). m/z: [M+H+] calcd for C38H49N3O4Si 640.4. Found 640.6.

後処理

  1. customto form a homogeneous solution
  2. temperatureThe reaction mixture was maintained at 140° C. for 10 min
  3. temperaturecooled to room temperature
  4. stirringThe reaction was stirred until all solids
  5. dissolutiondissolved
  6. customtransferred to a separatory funnel
  7. washThe organic layer was washed with water (17 mL)
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-ce7c0721498a4dd4aeb7f55d82112343
出典データセット
uspto-grants-2010_12
特許番号
US07846973B2

関連ノート

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