Triethylamine → HCID 54264483, 화합물

HRID 1768913노트

반응식

HRID 1768913 반응식
[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13](Cl)(=[O:15])=[O:14].Cl.[C:19]([O:23][C:24](=[O:34])[C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30](=[O:33])[CH2:31][NH2:32])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[C:19]([O:23][C:24](=[O:34])[C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30](=[O:33])[CH2:31][NH:32][S:13]([C:8]1[C:9]2[C:4](=[C:3]([N:2]([CH3:17])[CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:15])=[O:14])([CH3:22])([CH3:20])[CH3:21]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 57383535tert-Butyl glycyl-L-prolinate--hydrogen chloride (1/1)

생성물 1

HCID 54264483HCID 54264483, 화합물수율 87.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

5-Dimethylamino-l-naphthalenesulfonyl chloride (5.10 g, 18.9 mmol) was added in portions to a well-stirred solution of glycyl-L-proline tert-butyl ester hydrochloride (5.00 g, 18.9 mmol) and triethylamine (5.20 mL, 37.8 mmol) in dry tetrahydrofuran (175 mL). The mixture was stirred at room temperature for 4 hours before it was diluted with ethyl acetate and washed successively with saturated sodium bicarbonate solution and brine. Following drying and solvent evaporation, the residue was chromatographed on silica gel (gradient elution with first 40% ethyl acetate in hexanes followed by 50% ethyl acetate in hexanes) and furnished 7.62 g (87%) of the title compound as a fluorescent green foam, m.p. 60°-67° C.; 1H NMR (CDCl3) δ 8.51 (dd, J=8.5, 3.3 Hz, 1H), 8.30 (d, J=8.7 Hz, 1H), 8.21-8.16 (m, 1H), 7.58-7.43 (m, 2H), 7.15 (d, J=7.4 Hz, 1H), 5.85-5.79 (m, 1H), 4.27-4.23 (m, 1H), 3.76-3.62 (m, 2H), 3.48-3.21 (m, 2H), 2.84 (s, 6H), 2.10-1.75 (m, 4H), 1.33 and 1.32 (2s, 9H); 13C NMR (CDCl3) ppm 170.84, 170.45, 165.84, 165.46, 152.04, 134.31, 134.16, 130.79, 130.16, 130.12, 129.87, 129.52, 129.47, 128.77, 123.23, 123.17, 119.22, 119.13, 115.59, 83.00, 81.82, 59.99, 59.38, 46.97, 45.98, 45.64, 44.69, 44.58, 31.41, 29.13, 28.05, 27.96, 24.49, 23.80, 22.36; IR (KBr, cm-1) 3266, 2978, 2942, 2876, 2834, 1736, 1658, 1456, 1440, 1370, 1330, 1148, 792, 626, 574; MS m/z (MH+) calcd 461.1984, obsd 461.1982.

후처리

  1. washwashed successively with saturated sodium bicarbonate solution and brine
  2. customFollowing drying
  3. customsolvent evaporation
  4. customthe residue was chromatographed on silica gel (gradient elution with first 40% ethyl acetate in hexanes followed by 50% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-0744f8bbf9a747d19cc35affc60c72c1
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380713

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