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Triethylamine → Trans-2-[(tertiary-butylcarbonyloxy)methyloxycarbonyl]-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

HRID 484461
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HRID 484461 반응식
[C:1]([C@H:4]1[CH2:13][C@H:12]([NH:14][C:15]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[C:11]2[C:6](=[CH:7][C:8]([Cl:25])=[CH:9][C:10]=2[Cl:24])[NH:5]1)([OH:3])=[O:2].[CH2:26](N(CC)CC)C.IC[CH2:35][C:36]([CH3:41])([CH3:40])[C:37]([O-:39])=[O:38]>O1CCCC1>[C:36]([C:37]([O:39][CH2:26][O:2][C:1]([C@H:4]1[CH2:13][C@H:12]([NH:14][C:15]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:16])[C:11]2[C:6](=[CH:7][C:8]([Cl:25])=[CH:9][C:10]=2[Cl:24])[NH:5]1)=[O:3])=[O:38])([CH3:41])([CH3:40])[CH3:35]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 15168526Trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinolineHCID 86639330HCID 86639330, 화합물

생성물 1

HCID 86747049Trans-2-[(tertiary-butylcarbonyloxy)methyloxycarbonyl]-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline수율 55.7%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

To a solution of trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline (0.06 g, 0.16 mmol, Example 34) in tetrahydrofuran (5 ml) was added triethylamine (0.027 ml, 0.19 mmol) followed by a solution of iodomethylpivalate (0.06 g, 0.24 mmol) in tetrahydrofuran (2 ml). This mixture was stirred at room temperature for 4 hours. The solvent was removed under vacuum and the residue obtained was purified by flash chromatography (using ethyl acetate in hexane as eluent) to give the title compound (0.044 g), m.p. 162.4°-163° C. δ (360 MHz, DMSO) 1.41 (9H, s, C(CH3)3, 1.66 (1H, ddd, J=13.4, 12.6 and 3.8 Hz, CHACHBHCCHD), 2.12 (1H, dm, J=13.4 Hz, CHACHBHCCHD), 3.41 (2H, NHCOCH2Ph), 3.97 (1H, dd, J=12.6 and 3.8 Hz, CHACHBHCCHD), 5.02 (1H, m, CHACHBHCCHD), 5.81 (2H, 2d, J=5.9 Hz, CO2CH2CO), 6.71 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.86 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.97 (1H, bs, ArNH), 7.26 (5H, m, ArH), 8.45 (1H, d, J=7.1 Hz, CHDNHCO); m/e (CI+) 493 (M+1). Found C, 58.37; H, 5.33; N, 5.69; C24H26Cl2N2O5 requires C, 58.43; H, 5.31; N, 5.68%.

후처리

  1. customThe solvent was removed under vacuum
  2. customthe residue obtained
  3. customwas purified by flash chromatography (using ethyl acetate in hexane as eluent)

출처 및 근거

ORD 기록
ord-0cc2c5f1d83043c7a62dd4271fccd3fc
출처 데이터셋
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05231102

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