Triethylamine → HCID 86744377, compound

HRID 1110462Notes

Reaction equation

HRID 1110462 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH2:7]([O:9][C:10](=[O:59])[C@H:11]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=1)[NH:12][C:13]([C:15]1([CH2:20][C@H:21]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:22][NH:23][C:24](=[O:43])[C@H:25]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14])[CH3:8].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:7]([O:9][C:10](=[O:59])[C@H:11]([CH2:51][C:52]1[CH:53]=[CH:54][C:55]([O:58][C:2]([O:4][CH2:5][CH3:6])=[O:3])=[CH:56][CH:57]=1)[NH:12][C:13]([C:15]1([CH2:20][C@H:21]([C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[CH2:22][NH:23][C:24](=[O:43])[C@H:25]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14])[CH3:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 86744378HCID 86744378, compound

Product 1

HCID 86744377HCID 86744377, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroformate (0.1093 g, 1.007 mmol) was added to an ice-cooled solution of N-{1-[3-(N2 -methanesulphonyl-N6 -t-butyloxycarbonyl-(S)-lysylamino)-2-(S)-t-butyloxycarbonylpropyl]-1-cyclopentanecarbony}-(S)-tyrosine-ethyl ester (0.7041 g, 0.916 mmol), triethylamine (0.2781 g, 2.75 mmol and 4-dimethylaminopyridine (0.0112 g in dry dichloromethane (20 ml). After 30 minutes the ice-cooling was removed and the reaction stirred overnight at room temperature. The solvent was then evaporated under reduced pressure and the residual oil partitioned between ethyl acetate (50 ml) and 2N hydrochloric acid (50 ml). The phases were separated and the organic phase washed with saturated sodium bicarbonate solution (50 ml), then with saturated brine, (50 ml) and was finally dried over magnesium sulphate, before removing the solvent under reduced pressure to give the crude product as an oil. Chromatography over silica gel, eluting with mixtures of dichloromethane and diethyl ether gave the title compound as a white foam (0.367 g, 48%). Found: C,56.68; H,7.36; N,6.65. C39H64N4O13S requires C,56.50; H,7.78; N,6.76%.

Workup

  1. customwas removed
  2. customThe solvent was then evaporated under reduced pressure
  3. customthe residual oil partitioned between ethyl acetate (50 ml) and 2N hydrochloric acid (50 ml)
  4. customThe phases were separated
  5. washthe organic phase washed with saturated sodium bicarbonate solution (50 ml)
  6. dry with materialwith saturated brine, (50 ml) and was finally dried over magnesium sulphate
  7. custombefore removing the solvent under reduced pressure
  8. customto give the crude product as an oil
  9. washChromatography over silica gel, eluting with mixtures of dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-269570b7941d476bb3aa155db5840476
Source dataset
uspto-grants-1990_12
Patent number
US04975444

Reaction notes

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