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Acetic Acid → carbonic acid (2S,4S)-2-tert-butylcarbonylamino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-5-methyl-hexylester tert-butyl ester

HRID 1099322
ノート
印刷プレビュー

反応式

HRID 1099322 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:3]=1.C([Li])[CH2:17][CH2:18][CH3:19].C(O[C:26]([N:28]1[C@H:32]([CH2:33][O:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][C@@H:30]([CH:42]([CH3:44])[CH3:43])[C:29]1=[O:45])=[O:27])(C)(C)C.[C:46](O)(=O)C>O1CCCC1.CCCCCC>[C:38]([O:37][C:35](=[O:36])[O:34][CH2:33][C@@H:32]([NH:28][C:26]([C:18]([CH3:17])([CH3:19])[CH3:46])=[O:27])[CH2:31][C@H:30]([C:29](=[O:45])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:3]=1)[CH:42]([CH3:43])[CH3:44])([CH3:39])([CH3:40])[CH3:41]
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 176Acetic AcidHCID 214587114-Bromo-1-methoxy-2-(3-methoxypropoxy)benzeneHCID 58298428(3S,5S)-5-tert-butoxycarbonyloxymethyl-3-isopropyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

生成物 1

HCID 66813799carbonic acid (2S,4S)-2-tert-butylcarbonylamino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-5-methyl-hexylester tert-butyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A solution of 7.9 g of 4-bromo-1-methoxy-2-(3-methoxypropoxy)-benzene in 125 mL of tetrahydrofuran is cooled to −78° C. A solution of n-butyllithium (14.219 g of a 1.6 M solution in hexane) is added within 50 minutes. The reaction mixture is stirred for 90 minutes at −78° C. and treated slowly with 75 mL of a tetrahydrofuran solution of 8.93 g of (3S, 5S)-5-tert-butoxycarbonyloxymethyl-3-isopropyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester. The resulting reaction mixture is stirred for 3 hours at −78° C. Finally the temperature is raised to −40° C. and the mixture stirred for 45 minutes. Acetic acid (4 mL) was added and the solvent removed by evaporation. The residue is dissolved in 100 mL of ethyl acetate and washed with two 75 mL portions of saturated sodium bicarbonate solution followed by one portion of 150 mL of water. The organic phase was dried and the solvent removed to give an oil. Chromatography on silica-gel, eluting with hexane/ethyl acetate gives, after combination of the product containing fractions and removal of the solvent, affords the title compound as an oil.

後処理

  1. customThe resulting reaction mixture
  2. stirringis stirred for 3 hours at −78° C
  3. temperatureFinally the temperature is raised to −40° C.
  4. stirringthe mixture stirred for 45 minutes
  5. customthe solvent removed by evaporation
  6. dissolutionThe residue is dissolved in 100 mL of ethyl acetate
  7. washwashed with two 75 mL portions of saturated sodium bicarbonate solution
  8. customThe organic phase was dried
  9. customthe solvent removed
  10. customto give an oil
  11. washChromatography on silica-gel, eluting with hexane/ethyl acetate
  12. customgives
  13. additionafter combination of the product containing
  14. customfractions and removal of the solvent

出典と根拠

ORDレコード
ord-10831c9e4cb046bd824fb5bfdb30fabf
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08143416B2

反応ノート

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