Glutamic acid diethyl ester → Diethyl N-(4-ethynylbenzoyl)-L-glutamate

HRID 620101

반응식

HRID 620101 반응식
[C:1]1(NP(Cl)(=O)OC2C=CC=CC=2)C=CC=C[CH:2]=1.N[C@H](C(OCC)=O)CCC(OCC)=O.C([C:34]1[CH:55]=[CH:54][CH:53]=[CH:52][C:35]=1[C:36]([NH:38][C@H:39]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:37])#C.[K+].[Br-]>C(Cl)Cl.CO>[C:1]([C:54]1[CH:55]=[CH:34][C:35]([C:36]([NH:38][C@H:39]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:37])=[CH:52][CH:53]=1)#[CH:2]

참가 물질

7

반응물 4

HCID 73961Glutamic acid diethyl esterHCID 103959Phosphoramidochloridic acid, N-phenyl-, phenyl esterHCID 253877Potassium BromideHCID 18631716diethyl N-(ethynylbenzoyl)-L-glutamate

생성물 1

HCID 10936456Diethyl N-(4-ethynylbenzoyl)-L-glutamate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 0.55 g of 4-ethynylbenzoic acid (obtained from tert.-butyl 4-ethynylbenzoate in 84% yield by hydrolysis with trifluoroacetic acid) in 50 ml of anhydrous ether and 25 ml of anhydrous tetrahydrofuran is added 1.58 ml of triethylamine. This is followed by 1.00 g of phenyl N-phenylphosphoramidochloridate. After stirring the reaction mixture at room temperature under nitrogen for 0.5 hour, 0.90 g of diethyl L-glutamate is added in one portion. The mixture is allowed to stir for another 8 hrs. After a workup, the residue is subjected to column chromatography using a 1% methanol:methylene chloride mixture as the eluent. The major fraction isolated from the column contained 0.68 g (54%) of diethyl N-(ethynylbenzoyl)-L-glutamate as an oil which slowly solidified: NMR (CDCl3, 300 MHz) delta 1.25 (t, 3H, J=6.9 Hz), 1.33 (t, 3H, J=6.9 Hz), 2.11°-2.60 (m, 4H), 3.23 (s, 1H), 4.09 (q, 2H, J=6.9 Hz), 4.27 (1, 2H, J=6.9 Hz), 4.80 (m, 1H), 7.12 (d, 1H, J=7.2 Hz), 7.59 (d, 2H, J=8.4 Hz), 7.81 (d, 2H, J=8.4 Hz); IR (KBr) 3330, 3280, 2990, 1735, 1640, 1520, 1380, 1200, 1105, 1020, 855, and 770 cm -1.

후처리

  1. stirringto stir for another 8 hrs
  2. customThe major fraction isolated from the column

출처 및 근거

ORD 기록
ord-dae1e4235c70436c88a6765ba477b8ff
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04818819

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