Triethylamine → di-tert-butyl (2,3,4,5-tetrafluorobenzoyl)-L-glutamate

HRID 23610

반응식

HRID 23610 반응식
Cl.[NH2:2][C@H:3]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CCN(CC)CC.[F:27][C:28]1[C:36]([F:37])=[C:35]([F:38])[C:34]([F:39])=[CH:33][C:29]=1[C:30](Cl)=[O:31]>C(Cl)Cl>[F:27][C:28]1[C:36]([F:37])=[C:35]([F:38])[C:34]([F:39])=[CH:33][C:29]=1[C:30]([NH:2][C@H:3]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])=[O:31]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 208636Di-tert-butyl glutamate hydrochlorideHCID 27336892,3,4,5-Tetrafluorobenzoyl chloride

생성물 1

HCID 11270493di-tert-butyl (2,3,4,5-tetrafluorobenzoyl)-L-glutamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To an ice-cold solution of di-tert-butyl L-glutamate hydrochloride (6.6 g, 22.4 mmol) and Et3N (6.9 ml, 50 mmol) in dry CH2Cl2 (70 ml) was added, over a period of 1.5 hr, 2,3,4,5-tetrafluorobenzoyl chloride (5.0 g, 23.5 mmol) in dry CH2Cl2 (20 ml) and thirty minutes later the solution was allowed to warm to room temperature. Sixteen hours later the solution was washed with H2O, dried (MgSO4) and evaporated to dryness. 1H NMR δ 1.40+1.42 (2s, 18H, t-butyl), 1.85+1.95 (2m, 2H, CH2CH), 2.34 (t, 2H, CH2CO, J=7.5 Hz), 4.3 (m, 1H, CH), 7.57 (m, 1H, H6), 8.80 (d, 1H, NH, J=7.5 Hz); 19F NMR δ −138.6+139.0 (2m, 2F, F2+5), −152.4 (m, 1H, F4), −154.9 (t, 1F, F3, J=20 Hz).

후처리

  1. washSixteen hours later the solution was washed with H2O
  2. dry with materialdried (MgSO4)
  3. customevaporated to dryness

출처 및 근거

ORD 기록
ord-b2e52de445c646f1a9a2145db1d992a4
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852755B1

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