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

HRID 484461Notes

Reaction equation

HRID 484461 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-0cc2c5f1d83043c7a62dd4271fccd3fc
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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