L-Serine → Ethyl 2-cyanomethyl-2-phenylmethylpropanoate

HRID 1108365노트

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HRID 1108365 반응식
[C:1]1([CH2:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:16][C:17]#[N:18].C([N-]C(C)C)(C)C.[Li+].CN(P(N(C)C)(N(C)C)=O)C.N[C@H](C(O)=O)CO>C1COCC1>[C:1]1([CH2:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([CH2:16][C:8]([CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:18]

참가 물질

8

반응물 5

HCID 5951L-SerineHCID 11534BromoacetonitrileHCID 12679HexamethylphosphoramideHCID 562367Ethyl 2-methyl-3-phenylpropanoateHCID 2724682Lithium diisopropylamide

생성물 2

HCID 562367Ethyl 2-methyl-3-phenylpropanoateHCID 10704694Ethyl 2-cyanomethyl-2-phenylmethylpropanoate수율 135.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The reaction of ethyl 2-phenylmethylpropanoate (9.60 g, 50 mmol) with bromoacetonitrile (9.0 g, 75 mmol) in the presence of lithium diisopropylamide (prepared by treating diisopropylamine (6.06 g, 60 mmol) with butyllithium in hexanes (2.5 M, 24 mL, 60 mmol)) in THF (150 mL) and HMPA (4.3 mL, 25 mmol), as described above in the preparation of Example 4, gave 11.95 g of the crude product as a pale yellow colored liquid. Ethyl 2-phenylmethylpropanoate was prepared as in Spencer R W, Tam T F, Thomas E, Robinson V J, Krantz A (1986) "Ynenol lactones: Synthesis and investigation of reactions relevant to their inactivation of serine proteases" J. Am. Chem. Soc., 108 5589-5597. Flash chromatography over silica gel (hexanes-CH2Cl2, 3:2) afforded 7.86 g (68%) of the nitrile as a colorless viscous liquid. Analytical sample was prepared by bulb-to-bulb distillation (pot temp. 110-115° C. (0.9 mmHg)).

후처리

  1. customas described above in the preparation of Example 4
  2. customgave 11.95 g of the crude product as a pale yellow colored liquid

출처 및 근거

ORD 기록
ord-e72d74b513c34a1ea5a17edc4cc61807
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066666

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