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

HRID 1428204Notes

Reaction equation

HRID 1428204 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-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-oxo-1,6-dihydro-pyridazine-4-carboxylic acid (10.5 g, 74.9 mmol), TBTU (25.3 g, 78.7 mmol), 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, 74.9 mmol) 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 ethyl acetate. This solution was washed twice with 5% sodium hydrogen carbonate solution, then dried and evaporated down.

Workup

  1. customwas evaporated to dryness in vacuo
  2. stirringthe residue was stirred with 200 mL ethyl acetate
  3. washThis solution was washed twice with 5% sodium hydrogen carbonate solution
  4. customdried
  5. customevaporated down

Sources & evidence

ORD record
ord-414d2fa178884a57982aed4d3d76b8ca
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

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