Triethylamine → HCID 131728263, compound

HRID 499696Notes

Reaction equation

HRID 499696 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:40])[NH:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:22](=[O:39])[CH2:23][C:24]([CH3:38])([CH3:37])[CH2:25][C@H:26]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][OH:28])[CH2:13]1.S(=O)(=O)=O.N1C=CC=CC=1>C(Cl)Cl.CS(C)=O>[CH3:8][O:9][C:10](=[O:40])[NH:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:22](=[O:39])[CH2:23][C:24]([CH3:38])([CH3:37])[CH2:25][C@H:26]([NH:29][C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH:27]=[O:28])[CH2:13]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 91472268HCID 91472268, compound

Product 1

HCID 131728263HCID 131728263, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.10 ml of triethylamine are added to a solution of 2.34 g of [1-(5(S)-tert-butoxycarbonylamino-6-hydroxy-3,3-dimethyl-hexanoyl)-1,2,3,4-tetrahydro-quinolin-3(R,S)-yl]-carbamic acid methyl ester in 20 ml of methylene chloride under argon at 0° C. The mixture is stirred for 5 minutes at 0° C. and then a solution of 2.65 g of pyridine sulfur trioxide in 12 ml of dimethylsulfoxide is added dropwise at 0-5° C. over 1 hour. The mixture is stirred at 0-5° C. for 30 minutes and then ice water is added dropwise to the mixture at 0-10° C. The mixture is stirred at 10° C. for 10 minutes and then extracted with methylene chloride (3×). The combined organic layers are washed successively with 10% aqueous sodium hydrogensulfate solution, water, 10% aqueous sodium bicarbonate solution and brine, dried over sodium sulphate, filtered and concentrated. The title compound is obtained as a white solid. Rf=0.44 (3:1 EtOAc-heptane); Rt=4.17 (gradient I).

Workup

  1. stirringThe mixture is stirred at 0-5° C. for 30 minutes
  2. stirringThe mixture is stirred at 10° C. for 10 minutes
  3. extractionextracted with methylene chloride (3×)
  4. washThe combined organic layers are washed successively with 10% aqueous sodium hydrogensulfate solution, water, 10% aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4f93c0eb0bdc44efa056294fcc275165
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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