Triethylamine → HCID 19608249, compound

HRID 745111Notes

Reaction equation

HRID 745111 reaction equation
C(OC([NH:8][CH2:9][C:10](O)=[O:11])=O)(C)(C)C.P(C#N)(OCC)(OCC)=O.[NH2:23][CH:24]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]([C:35](=[O:52])[C:36]2[CH:41]=[CH:40][C:39]([NH:42][C:43](=[O:51])[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[CH3:50])=[CH:38][CH:37]=2)[CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C>CN(C)C=O>[NH2:8][CH2:9][C:10]([NH:23][CH:24]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]([C:35](=[O:52])[C:36]2[CH:41]=[CH:40][C:39]([NH:42][C:43](=[O:51])[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[CH3:50])=[CH:38][CH:37]=2)[CH2:27][CH2:26][CH2:25]1)=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 10692311HCID 10692311, compound

Product 1

HCID 19608249HCID 19608249, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of t-butoxycarbonylglycine (0.84 g) in dimethylformamide (20 ml) are added diethyl cyanophosphate (0.73 ml) and 5-amino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.74 g), and further thereto is added triethylamine (1.8 ml) under ice-cooling. The mixture is stirred for 30 minutes, and then stirred at room temperature overnight. The reaction solution is concentrated and water is added to the resulting residue. The precipitated crystal is collected by filtration, washed with water, and recrystallized from ethyl acetate to give 5-(2-aminoacetylamino)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (E) (0.16 g). Separately, the liltrate is concentrated and purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1), and recrystallized from diethyl ether to give 5-[2-(t-butoxycarbonylamino)acetylamino]-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (F) (0.19 g).

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature overnight
  3. concentrationThe reaction solution is concentrated
  4. additionwater is added to the resulting residue
  5. filtrationThe precipitated crystal is collected by filtration
  6. washwashed with water
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-607f9d0cce8d434aaf150b0a781924b8
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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