Aminoisobutyric acid → HCID 22916684, compound
Reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3](O)=O.C(N(CC)CC)C.FC(F)(F)[C:17](OCC)=[O:18].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:49][CH2:50][C:51]1[S:52][CH:53]=[CH:54][N:55]=1>>[CH:17]([NH:1][C:2]([C:3]1[N:55]2[C:51]([S:52][CH:53]=[CH:54]2)=[CH:50][N:49]=1)([CH3:7])[CH3:6])=[O:18]Participants
Procedure
To 2.5 g (0.024m mole) of 2-amino-2-methylpropanoic acid was added under ice-cooling 17 ml (0.122 mole) of triethylamine, followed by 15 ml (0.14 mole) of ethyl trifluoroacetate, and the mixture was stirred for 1 hour. Six milliliter (0.05 mole) of ethyl trifluoroacetate was added, and the mixture was further stirred for 20 hours. The reaction mixture was concentrated to dryness under reduced pressure. To the solution of the residue thus obtained in methylene chloride (20 ml) was added 5 g (0.036 mole) of 1-hydroxybenzotriazole at a temperature of 3° C., followed by 38 ml (0.036 mole) of 1.0M dicyclohexylcarbodiimide and 2.85 g (0.025 mole) of 2-aminomethylthiazole. The mixture was treated in the same manner as in Preparation 16 (a) to give 4.9 g of the title compound. Yield 66%. NMR (CDCl3) δ: 1.71 (6H, s), 4.80 (2H, d, J=5.6 Hz), 7.03 (1H, brs), 7.33 (1H, d, J=3.3 Hz), 7.72 (1H, d, J=3.3 Hz), 7.81 (1H, brs).
Workup
- stirringthe mixture was further stirred for 20 hours
- concentrationThe reaction mixture was concentrated to dryness under reduced pressure
- customTo the solution of the residue thus obtained in methylene chloride (20 ml)
Sources & evidence
- ORD record
- ord-a851ce9be1a243af88a29265650b898d
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05663162
Reaction notes
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