N,N’-1,2-乙烷基双[N-(羧甲基)-甘氨酸]三钠盐 → Racemic ethyl cis-3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate

HRID 2078487

反应方程式

HRID 2078487 反应方程式
[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:9])[CH3:8])(=[O:3])[CH3:2].[N+](=C[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-].[CH2:18](N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC([O-])=O.[Na+].[Na+].[Na+].CC[C@@H]1N2C(N(C3C=CC(F)=CC=3)C(=O)[C@H]2CC2C3C(NC1=2)=CC=CC=3)=O>C(OCC)(=O)C.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)C([O-])=O)C=CC=CC=1.[Rh+3].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)C([O-])=O)C=CC=CC=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)C([O-])=O)C=CC=CC=1>[C:1]([O:4][CH2:5][C@@H:6]1[C@H:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]1([CH3:18])[CH3:9])(=[O:3])[CH3:2]

参与物

7

反应物 4

HCID 9008N,N’-1,2-乙烷基双[N-(羧甲基)-甘氨酸]三钠盐HCID 12192重氮乙酸乙酯HCID 14489梨醇酯HCID 24978618trans-Body

产物 1

HCID 67120924Racemic ethyl cis-3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate

试剂、催化剂与溶剂 2

HCID 71464060Rhodium triphenyl acetate催化剂HCID 8857乙酸乙酯溶剂2 次

反应条件

温度
50 °C

实验过程

Rhodium triphenylacetate, 6.78 mg (0.01 mmol), was dissolved in 9.0 g of ethyl acetate, and 2.56 g (20.0 mmol) of 1-acetoxy-3-methyl-2-butene was added, then, the temperature thereof was raised to 50° C. Into this solution, a solution composed of 1.14 g (10.0 mmol) of ethyl diazoacetate and 3.6 g of ethyl acetate was dropped over a period of 2 hours, and the mixture was, thermally kept at the same temperature for 0.5 hours. To this solution was added an aqueous solution containing 0.5 mol of trisodium ethylenediaminetetraacetate per liter and the solution was mixed and separated, and a solution containing 1.82 g of ethyl 3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate was obtained (yield based on ethyl diazoacetate: 84.8%). The cis body/trans body ratio was 72/28.

后处理

  1. additionwas dropped over a period of 2 hours
  2. additionTo this solution was added an aqueous solution
  3. additionthe solution was mixed
  4. customseparated
  5. additiona solution containing 1.82 g of ethyl 3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate
  6. customwas obtained
  7. custom(yield based on ethyl diazoacetate: 84.8%)

来源与证据

ORD记录
ord-d0790c9840c94fa5bdb44412e7d5bb07
来源数据集
uspto-grants-2011_04
专利号
US07928253B2

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