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HRID725616

反应详情

EQUATION

反应方程式

HRID 725616 的结构方程式

REACTANTS

反应物

3
结构：[N-]=[N+]=[N-]
HCID33558

Azide

N3-

结构：CCCC[N+](CCCC)(CCCC)CCCC.[N-]=[N+]=[N-]
HCID5743232

1-Butanaminium, N,N,N-tributyl-, azide

C16H36N4

结构：CC(C)[C@@H]1C[C@@H]([C@H](Br)C[C@H](C(=O)N2C(=O)OC[C@@H]2Cc2ccccc2)C(C)C)OC1=O
HCID54147056

(4S)-3-[(2S,4R)-4-Bromo-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-2-oxazolidinone

C24H32BrNO5

PRODUCTS

生成物

1
结构：CC(C)[C@@H]1C[C@@H]([C@H](C[C@H](C(=O)N2C(=O)OC[C@@H]2Cc2ccccc2)C(C)C)N=[N+]=[N-])OC1=O
HCID53385507

(4S)-3-[(2S,4S)-4-azido-4-[(2S,4S)-5-oxo-4-propan-2-yloxolan-2-yl]-2-propan-2-ylbutanoyl]-4-benzyl-1,3-oxazolidin-2-one

C24H32N4O5

AUXILIARIES

试剂、催化剂与溶剂

1
结构：Cc1ccccc1
溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

13.6 g of freshly dried tetrabutylammonium azide are added to a solution, stirred at room temperature, of 17.8 g of 3(S)-isopropyl-5(S)-{1(R)-bromo-4-methyl-3(S)-[(4(S)-benzyloxazolidin-2-on-3-yl)-carbonyl]-pentyl}-tetrahydrofuran-2-one in 180 ml of toluene, and a further 10 g of the azide are added in the course of 160 hours' stirring at room temperature. The reaction mixture is then partitioned between ethyl acetate and water (2×) and saturated sodium chloride solution (1×). The organic phases are combined, dried over sodium sulfate and concentrated. The title compound is obtained from the evaporation residue by means of FC (hexane/ethyl acetate=8:2) and crystallisation from diethyl ether/hexane: m.p.=102°-103° C.; Rf (hexane/ethyl acetate=8:2)=0.2; HPLC Rt =18.55 minutes; FAB-MS (M+H)+ =457.

WORKUP

后处理

  1. customThe reaction mixture is then partitioned between ethyl acetate and water (2×) and saturated sodium chloride solution (1×)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated