Phosphate → HCID 70547083, 화합물

HRID 1680129

반응식

HRID 1680129 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 70547083HCID 70547083, 화합물

시약·촉매·용매 2

HCID 23994Zinc촉매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e731f7a5510b48b19e060e69ea687881
출처 데이터셋
uspto-grants-1981_06
특허 번호
US04272439

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