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HRID264920

反应详情

EQUATION

反应方程式

HRID 264920 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 (2x) and saturated sodium chloride solution (1x). 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 (2x) and saturated sodium chloride solution (1x)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated