N-Acetyl-L-Cysteine → (1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-hydroxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate

HRID 2271285

反応式

HRID 2271285 の反応式
[C:1](N[C@H](C(O)=O)CS)(=O)[CH3:2].O.O.O.O.O.O.O.O.O.O.B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].C1([SeH-](C2C=CC=CC=2)=[Se])C=CC=CC=1.[O:63]1[CH:69]2[CH:64]1[C:65](=[O:74])[CH:66]1[CH:68]2[C:67]1([F:73])[C:70]([O-:72])=[O:71]>O.C(O)C.O.O1CCCC1>[F:73][C:67]1([C:70]([O:72][CH2:1][CH3:2])=[O:71])[CH:66]2[CH:68]1[CH:69]([OH:63])[CH2:64][C:65]2=[O:74]

参加物

8

反応物 4

HCID 12035N-Acetyl-L-CysteineHCID 86618040Sodium tetraborate decahydrate; Solubor; Solubor DF; Three Elephant; TincalHCID 867576963,4-Epoxy-6-fluoro-2-oxobicyclo [3.1.0]hexane-6-carboxylateHCID 178528034HCID 178528034、化合物

生成物 1

HCID 69853523(1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-hydroxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 19096565Water ethanol溶媒

反応条件

温度
38 °C

実験手順

Under a nitrogen atmosphere, 23.2 g of N-acetyl-L-cystein, 54.3 g of sodium tetraborate decahydrate and 0.7 g of diphenyldiselenide were suspended in 450 ml of a water-ethanol (1:1) mixture solution which had been deaerated. 9.5 g of (1RS,3RS,4RS,5SR,6RS)ethyl (3,4-epoxy-6-fluoro-2-oxobicyclo [3.1.0]hexane-6-carboxylate dissolved into 225 ml of tetrahydrofuran was added thereto, and this was stirred at room temperature for one day, at 38° C. for 12 hours, and at 85° C. for 5 hours. After the reaction solution was cooled down to room temperature, it was poured into water and extracted three times with diethyl ether. The obtained organic layers were consolidated and dried over anhydrous sodium sulfate. After filtering off the desiccant, concentration of the filtrate was carried out under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=3:1 to 1:1), yielding 3.9 g of (1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-hydroxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate. The proton NMR and mass spectrograph data are shown below.

後処理

  1. additionwas added
  2. waitat 85° C. for 5 hours
  3. temperatureAfter the reaction solution was cooled down to room temperature
  4. extractionextracted three times with diethyl ether
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtering off the desiccant, concentration of the filtrate
  7. customThe residue was purified by column chromatography (silica gel: Wako gel (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=3:1 to 1:1)

出典と根拠

ORDレコード
ord-9330732d1e6a40969f6c8e9d04239b4e
出典データセット
uspto-grants-2001_12
特許番号
US06333428B1

関連ノート

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