Phosphate → HCID 70547083、化合物

HRID 1680129

反応式

HRID 1680129 の反応式
[CH3:1][C:2]1([CH3:13])[C@H:6]([C:7]#[N:8])[N:5]2[C:9](=[O:12])[C@H:10](Br)[C@H:4]2[S:3]1.O1CCCCC1OC1C=CC(C=O)=CC=1.P([O-])([O-])([O-])=O>O1CCCC1.[Zn]>[CH3:1][C:2]1([CH3:13])[C@H:6]([C:7]#[N:8])[N:5]2[C:9](=[O:12])[CH2:10][C@H:4]2[S:3]1

参加物

6

反応物 3

HCID 1061PhosphateHCID 112527364-(2-Tetrahydro-2H-pyranoxy)benzaldehydeHCID 129447132,2-Dimethyl-3alpha-cyano-6alpha-bromopenam

生成物 1

HCID 70547083HCID 70547083、化合物

試薬・触媒・溶媒 2

HCID 23994Zinc触媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

Activated mossy zinc (500 mg) and zinc dust (100 mg) are added to a solution of 2,2-dimethyl-3α-cyano-6α-bromopenam (522 mg, 2 mmol) and p-(2-tetrahydropyranyloxy)benzaldehyde (750 mg, 3.75 mmol) prepared according to E. Piers, W. deWaal and R. W. Britton, J. Am. Chem. Soc., 93, 5113 (1971) in 1 ml of dry tetrahydrofuran. After stirring vigorously at 50° for 3 hrs., the mixture is allowed to cool and 1 ml of pH 5 phosphate buffer is added. After standing for 10 min., the solids are removed by filtration and washed thoroughly with ethyl acetate. The filtrate is extracted with ethyl acetate. The combined extracts are washed with phosphate buffer and saturated sodium chloride, dried with sodium sulfate and the solvents removed by evaporation. The crude material is purified by chromatography on 60 g of silica gel using 40% acetone/chloroform as eluant to afford 2,2-dimethyl-3α-cyanopenam as a by-product melting at 73°- 75° C. and a mixture of 2,2-dimethyl-3α-cyano-6α-[p-(2-tetrahydropyranyloxy)-α-hydroxybenzyl]penam and 2,2-dimethyl-3α-cyano-6β-[p-(2-tetrahydropyranyloxy)-α-hydroxybenzy]-penam. Separation of the 6α-and 6β-compounds is effected by PLC (10% acetone/toluene; two developments) providing the individual 6α- and 6β-compounds.

後処理

  1. customprepared
  2. temperatureto cool
  3. waitAfter standing for 10 min.
  4. customthe solids are removed by filtration
  5. washwashed thoroughly with ethyl acetate
  6. extractionThe filtrate is extracted with ethyl acetate
  7. washThe combined extracts are washed with phosphate buffer and saturated sodium chloride
  8. dry with materialdried with sodium sulfate
  9. customthe solvents removed by evaporation
  10. customThe crude material is purified by chromatography on 60 g of silica gel using 40% acetone/chloroform as eluant

出典と根拠

ORDレコード
ord-e731f7a5510b48b19e060e69ea687881
出典データセット
uspto-grants-1981_06
特許番号
US04272439

関連ノート

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