Sodium Bicarbonate → (1R,2R,3S,5R,6R)-2-amino-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

HRID 130507ノート

反応式

HRID 130507 の反応式
CP(C)C.O1CCCC1.[CH2:10]([O:12][C:13]([C@:15]1([N:28]=[N+]=[N-])[C@@H:20]([OH:21])[CH2:19][C@@H:18]2[C@H:16]1[C@@:17]2([F:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:14])[CH3:11].C(=O)([O-])O.[Na+]>O1CCCC1.O.C(OCC)C>[CH2:10]([O:12][C:13]([C@:15]1([NH2:28])[C@@H:20]([OH:21])[CH2:19][C@@H:18]2[C@H:16]1[C@@:17]2([F:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:14])[CH3:11]

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 11185694(1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl esterHCID 86589763trimethylphosphine THF

生成物 1

HCID 11288856(1R,2R,3S,5R,6R)-2-amino-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester収率 72.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

0.89 mL of a solution of 1M trimethylphosphine/tetrahydrofuran was added to 245 mg of (1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 7.0 mL of tetrahydrofuran and 0.7 mL of water, and the mixture was stirred for 12 hours at room temperature. After the mixture was diluted with 14 mL of diethyl ether, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and the mixture was stirred for 1 hour at room temperature. After separation, the aqueous layer was extracted twice with chloroform. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure The residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: chloroform-ethanol=50:1), thereby yielding 163 mg of (1R,2R,3S,5R,6R)-2-amino-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

後処理

  1. customAfter separation
  2. extractionthe aqueous layer was extracted twice with chloroform
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure The residue
  7. customwas purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: chloroform-ethanol=50:1)

出典と根拠

ORDレコード
ord-7c28b5994f68413682f3b760143cf0e1
出典データセット
uspto-grants-2008_06
特許番号
US07381746B2

反応ノート

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