Triethylamine → n-Butyl(S)-3-[(6-oxo-1,6-dihydro-pyridazine-4-carbonyl)-amino]-tetrahydrofuran-3-carboxylate

HRID 1396495Notes

Reaction equation

HRID 1396495 reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]([OH:10])=O)=[CH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[NH2:40][C@@:41]1([C:46]([O:48][CH2:49][CH2:50][CH2:51][CH3:52])=[O:47])[CH2:45][CH2:44][O:43][CH2:42]1>C1COCC1.CN(C=O)C>[O:1]=[C:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]([NH:40][C@@:41]2([C:46]([O:48][CH2:49][CH2:50][CH2:51][CH3:52])=[O:47])[CH2:45][CH2:44][O:43][CH2:42]2)=[O:10])=[CH:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 123762656-Oxo-1,6-dihydropyridazine-4-carboxylic acidHCID 59621155Butyl (S)-3-aminotetrahydrofuran-3-carboxylate

Product 1

HCID 68023757n-Butyl(S)-3-[(6-oxo-1,6-dihydro-pyridazine-4-carbonyl)-amino]-tetrahydrofuran-3-carboxylateYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-oxo-1,6-dihydro-pyridazine-4-carboxylic acid (11.5 g), TBTU (25.3 g), triethylamine (20.9 mL) and 40 mL DMF in 200 mL THF was stirred for 30 minutes at ambient temperature. Then n-butyl (S)-3-amino-tetrahydrofuran-3-carboxylate (14.0 g) was added and the mixture was stirred further overnight. For working up the mixture was evaporated to dryness in vacuo and the residue was stirred with 200 mL of ethyl acetate. This solution was washed twice with 5% sodium hydrogen carbonate solution, then dried and evaporated down. The product was thus obtained in a yield of 90% of theory.

Workup

  1. customwas evaporated to dryness in vacuo
  2. stirringthe residue was stirred with 200 mL of ethyl acetate
  3. washThis solution was washed twice with 5% sodium hydrogen carbonate solution
  4. customdried
  5. customevaporated down
  6. customThe product was thus obtained in a yield of 90% of theory

Sources & evidence

ORD record
ord-9c2df8e642954f09a83020ff72633e89
Source dataset
uspto-grants-2014_12
Patent number
US08901127B2

Reaction notes

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