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

HRID 1955689노트

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HRID 1955689 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 (2.5M, 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-36707f9b22384f84bfcb2a676a00cf22
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05776959

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