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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 1487482
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HRID 1487482 반응식
[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]
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참가 물질

7

반응물 4

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

생성물 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

시약·촉매·용매

2
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6473c5957ba347e8a9f8e846fb91cc8d
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09428528B2

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