Tert-butoxycarbonylalanine → HCID 68158042, compound

HRID 243163Notes

Reaction equation

HRID 243163 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.C1C=NC2N(O)N=NC=2C=1.[F:36][C:37]1[CH:38]=[C:39]([NH:44][C:45]2[N:50]=[CH:49][CH:48]=[CH:47][N:46]=2)[C:40]([NH2:43])=[CH:41][CH:42]=1>C(Cl)Cl.CN(C=O)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:11](=[O:13])[NH:43][C:40]1[CH:41]=[CH:42][C:37]([F:36])=[CH:38][C:39]=1[NH:44][C:45]1[N:46]=[CH:47][CH:48]=[CH:49][N:50]=1)[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68157528HCID 68157528, compound

Product 1

HCID 68158042HCID 68158042, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)-L-alanine (199 mg, 1.05 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (222 mg, 1.15 mmol) and HOAt (143 mg, 1.05 mmol) were added to 4-fluoro-N2-pyrimidin-2-yl-benzene-1,2-diamine (215 mg, 1.05 mmol) in DCM (8.0 ml) and DMF (800 μl) at 0° C. The reaction was stirred for 2 h then poured into water and the aqueous layer extracted with DCM (×3). The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The product was purified by chromatography (SiO2, 0-10% methanol/DCM) to yield the title compound (350 mg, 0.93 mmol, 89%). LCMS: RT 2.98 min [M+H]+ 376.1. 1H NMR (CDCl3, 300 MHz): δ 8.48 (1H, br s), 8.42 (2H, d, J=4.9 Hz), 7.69 (1H, br s), 7.50 (2H, m), 6.84 (1H, td, J 8.5, 2.9 Hz), 6.76 (1H, t, J=4.9 Hz), 5.01 (1H, br s), 4.28 (1H, qn, J=7.6 Hz), 1.44 (9H, s), 1.43 (3H, d, J=7.4 Hz).

Workup

  1. extractionthe aqueous layer extracted with DCM (×3)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by chromatography (SiO2, 0-10% methanol/DCM)

Sources & evidence

ORD record
ord-1c73f737375f4a96bd6e4a177de40896
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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