Triethylamine → HCID 19608249, compound

HRID 1603154Notes

Reaction equation

HRID 1603154 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 filtrate 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-1f417df72b6448fcaea8756033b209c5
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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