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Toluene → (5-{4-[(1R,2S)-2-(2,2-Dichloro-acetylamino)-3-fluoro-1-hydroxy-propyl]-phenyl}-oxazol-2-ylmethyl)-carbamic acid tert-butyl ester

HRID 1520480
ノート
印刷プレビュー

反応式

HRID 1520480 の反応式
[C:1]([O:5][C:6](=[O:8])[NH2:7])([CH3:4])([CH3:3])[CH3:2].[Cl:9][CH:10]([Cl:29])[C:11]([NH:13][C@H:14]([CH2:27][F:28])[C@H:15]([OH:26])[C:16]1[CH:21]=[CH:20][C:19]([Sn](C)(C)C)=[CH:18][CH:17]=1)=[O:12].[F-].[Cs+].[C:32]1([CH3:38])C=CC=CC=1>O.[Cu]I>[C:1]([O:5][C:6](=[O:8])[NH:7][CH2:10][C:11]1[O:12][C:32]([C:19]2[CH:20]=[CH:21][C:16]([C@@H:15]([OH:26])[C@H:14]([NH:13][C:11](=[O:12])[CH:10]([Cl:29])[Cl:9])[CH2:27][F:28])=[CH:17][CH:18]=2)=[CH:38][N:13]=1)([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1140TolueneHCID 25953Cesium fluorideHCID 77922tert-Butyl carbamateHCID 866953832,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-trimethylstannanyl-phenyl)-ethyl]-acetamide

生成物 1

HCID 86695438(5-{4-[(1R,2S)-2-(2,2-Dichloro-acetylamino)-3-fluoro-1-hydroxy-propyl]-phenyl}-oxazol-2-ylmethyl)-carbamic acid tert-butyl ester

試薬・触媒・溶媒

2
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 5-Bromo-oxazol-2-ylmethyl)-carbamic acid tert-butyl ester (0.035 g, 0.13 mmol) and 2,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-trimethylstannanyl-phenyl)-ethyl]-acetamide (0.05 g, 0.11 mmol) in dry toluene (2.0 mL) is added CsF (0.034 g, 0.22 mmol) followed by CuI (0.002 g, 0.011 mmol) at room temperature. The resulting reaction mixture is degassed with nitrogen for 30 minutes then Pd2(PPh3)Cl2 (0.008 g, 0.011 mmol) is added and heated in microwave at 100° C. for 30 min. Reaction mixture is diluted with water and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography eluting in 10% methanol in CH2Cl2 follow by second purification using preparative HPLC to give the title compound (0.006 g, pure). LC-Ms (m/z): [M−H]=476.0.

後処理

  1. customThe resulting reaction mixture
  2. customis degassed with nitrogen for 30 minutes
  3. customReaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialOrganic layer is dried over sodium sulphate, solvent
  6. customis evaporated in vacuo
  7. custompurified by column chromatography
  8. washeluting in 10% methanol in CH2Cl2
  9. customfollow by second purification

出典と根拠

ORDレコード
ord-b928a7459116488ab75ff32698234b75
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073894B2

反応ノート

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