L-Hydroxyproline → (2s,4r)-4-Hydroxy-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acid

HRID 458332ノート

反応式

HRID 458332 の反応式
[NH:1]1[CH2:9][C@H:7]([OH:8])[CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C(N1CCOCC1)C.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[S:28](Cl)(=[O:30])=[O:29].C([O-])(O)=O.[Na+]>C[Si](C)(C)N[Si](C)(C)C.C1COCC1.CCOCC.C(O)C>[OH:8][C@H:7]1[CH2:9][N:1]([S:28]([C:19]2[CH:20]=[CH:21][C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=2)(=[O:30])=[O:29])[C@H:2]([C:3]([OH:5])=[O:4])[CH2:6]1

参加物

9

反応物 4

HCID 5810L-HydroxyprolineHCID 71252-Naphthalenesulfonyl chlorideHCID 7525EthylmorpholineHCID 516892Sodium Bicarbonate

生成物 1

HCID 6363699(2s,4r)-4-Hydroxy-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acid収率 67.9%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 13838Hexamethyldisilazane溶媒

反応条件

温度
120 °C

実験手順

11 g (83.9 mmol) L-Hydroxyproline were dissolved in 110 ml hexamethyldisilazane and heated to 120° C. overnight, cooled to room temperature and evaporated. The oily residue was dissolved in 110 ml THF, 16.5 ml (79.7 mmol, 0.95 eq) N-ethyl-morpholine was added, followed by 18.25 g (79.7 mmol, 0.95 eq) 2-naphthalenesulfonyl chloride in 130 ml THF over a period of 60 min. The solution was stirred at RT for 50 h, 15 ml ethanol were added and the solution was stirred for 15 min. At that time 400 ml of Et2O and 250 ml of aqueous saturated NaHCO3 solution were added and the phases were separated. The aqueous layer was acidified and extracted with EtOAc, the combined organic layers were washed with brine, dried over MgSO4 and concentrated. 17.39 g (65%) (2S,4R)-4-hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid isolated as yellow solid, mp 140° C., MS: 321 (MH+).

後処理

  1. temperaturecooled to room temperature
  2. customevaporated
  3. dissolutionThe oily residue was dissolved in 110 ml THF
  4. stirringthe solution was stirred for 15 min
  5. customthe phases were separated
  6. extractionextracted with EtOAc
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-cea5cdd3e803416589ea81d494012952
出典データセット
uspto-grants-2007_03
特許番号
US07189756B2

反応ノート

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