Sodium hydride → 5-Oxo-4-prop-2-ynyl-piperazine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

HRID 1432923노트

반응식

HRID 1432923 반응식
[H-].[Na+].[CH3:3][O:4][C:5](=[O:27])[CH:6]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:7][N:8]([C:12](=[O:15])[CH2:13]Br)[CH2:9][C:10]#[CH:11]>C1COCC1>[CH3:3][O:4][C:5]([CH:6]1[CH2:7][N:8]([CH2:9][C:10]#[CH:11])[C:12](=[O:15])[CH2:13][N:16]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:27]

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 1317277242-Benzyloxycarbonylamino-3-(bromoactyl-prop-2-ynyl-amino)-propionic acid methyl ester

생성물 1

HCID 539714095-Oxo-4-prop-2-ynyl-piperazine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester수율 85.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (0.20 mg, 4.9 mmol) is added to a solution of 2-benzyloxycarbonylamino-3-(bromoactyl-prop-2-ynyl-amino)-propionic acid methyl ester (2.0 g, 4.8 mmol) in THF (50 mL) at 0° C. The solution is stirred for 40 minutes then quenched with saturated NH4Cl solution. The reaction mixture is concentrated in vacuo then diluted with CH2Cl2 and washed with brine. The organic layer is dried over, filtered and concentrated in vacuo. The crude product is purified by chromatography eluting with 50% EtOAc/hexanes to give the title product (1.4 g, 4.1 mmol). 1H NMR (CDCl3, 300 MHz) δ7.30 (m, 5H), 5.20 (s, 2H), 5.10 (m, 1H), 4.30 (dd, 1H), 4.25 (d, 2H), 4.08 (m, 1H), 4.00 (dd, 1H), 3.78 (dd, 1H), 3.78 (s, 3H), 2.25 (t, 1H).

후처리

  1. customthen quenched with saturated NH4Cl solution
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. additionthen diluted with CH2Cl2
  4. washwashed with brine
  5. customThe organic layer is dried over,
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by chromatography
  9. washeluting with 50% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-c339b6c7d91e4f9ca6963726f1fbf4b8
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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