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

HRID 484461
ノート
印刷プレビュー

反応式

HRID 484461 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-0cc2c5f1d83043c7a62dd4271fccd3fc
出典データセット
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05231102

反応ノート

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