Triethylamine → HCID 56611972, compound

HRID 987215Notes

Reaction equation

HRID 987215 reaction equation
C([O:5][C:6](=[O:38])[C@@H:7]([NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH2:8][NH:9][C:10]([C:12]1[CH:13]=[C:14]2[N:19]([C:20](=[O:22])[CH:21]=1)[CH:18]=[C:17]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])[CH:16]=[CH:15]2)=[O:11])(C)(C)C.C(N(CC)CC)C.[CH3:46][N:47]=[C:48]=[O:49]>C(#N)C>[C:32]1([S:29]([NH:28][C@@H:7]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[C:14]3[N:19]([C:20](=[O:22])[CH:21]=2)[CH:18]=[C:17]([O:23][CH2:24][CH2:25][CH2:26][NH:27][C:48]([NH:47][CH3:46])=[O:49])[CH:16]=[CH:15]3)=[O:11])[C:6]([OH:5])=[O:38])(=[O:30])=[O:31])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 86759195HCID 86759195, compound

Product 1

HCID 56611972HCID 56611972, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (S)-3-{[7-(3-amino-propoxy)-4-oxo-4H-quinolizine-2-carbonyl]-amino}-2-benzenesulfonylamino-propionic acid tert-butyl ester (10.0 mg, 0.015 mmol) in anhydrous acetonitrile (0.5 ml) were added triethylamine (4 μl, 0.030 mmol) and methyl isocyanate (1 μl, 0.015 mmol). The mixture was stirred for 5 minutes at 0° C. and 30 minutes at room temperature, quenched with water and extracted with dichloromethane (3x). The combined organic layers were dried (MgSC4) and concentrated to give 4.1 mg (81% yield) of desired product.

Workup

  1. customquenched with water
  2. extractionextracted with dichloromethane (3x)
  3. dry with materialThe combined organic layers were dried (MgSC4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d5473c60c3aa47d29362475df5b90356
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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