Triethylamine → HCID 178513962, compound

HRID 2413708Notes

Reaction equation

HRID 2413708 reaction equation
Br.Br.[NH2:3][C@H:4]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([NH2:17])=[O:16])=[O:12])[CH2:5][C:6]1[N:10]=[CH:9][NH:8][CH:7]=1.C(N(CC)CC)C>CN(C=O)C>[NH2:3][C@H:4]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([NH2:17])=[O:16])=[O:12])[CH2:5][C:6]1[N:10]=[CH:9][NH:8][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 178419276HCID 178419276, compound

Product 1

HCID 178513962HCID 178513962, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 27 ml of DMF was dissolved 2.18 g of L-histidyl-L-prolinamide dihydrobromide (4). The solution was cooled to -15° to -10° C. and 1.63 ml of triethylamine was added thereto. After reacting at this temperature for 20 minutes, the formed precipitates were filtered off to obtain a solution of L-histidyl-L-prolinamide. The solution was immediately used for the following synthesis. In a mixture of 14 ml of DMF and 14 ml of methylene chloride were dissolved 868 mg of compound (20 ) and 859 mg of HOBT and, 1.31 g of DCC was added to the solution under ice cooling. The mixture was reacted for 40 minutes. To the reaction mixture was added the foregoing DMF solution of L-histidyl-L-prolinamide. The reaction was performed at 0° to 4° C. overnight. The precipitates were filtered off and the filtrate was concentrated to dryness. The residue was subjected to column chromatography using silica gel. By eluting with chloroform-methanol-conc. ammonia water (80:20:2), 610 mg of Nα -(2-oxo-1-azetidinylacetyl)-L-histidyl-L-prolinamide (21) was obtained.

Workup

  1. temperatureThe solution was cooled to -15° to -10° C.
  2. customthe formed precipitates
  3. filtrationwere filtered off

Sources & evidence

ORD record
ord-8fe9878a11e1422b84cebb2c8c0eb52f
Source dataset
uspto-grants-1988_01
Patent number
US04719207

Reaction notes

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