Tert-butoxycarbonylalanine → HCID 68157566, compound

HRID 243154Notes

Reaction equation

HRID 243154 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:16]([NH:23][C@H:24]([C:26](O)=[O:27])[CH3:25])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:19]([O:18][C:16](=[O:17])[NH:23][C@H:24]([C:26](=[O:27])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][N:11]=1)[CH3:25])([CH3:20])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68157931HCID 68157931, compound

Product 1

HCID 68157566HCID 68157566, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-fluoro-N2-pyrimidin-4-ylbenzene-1,2-diamine (0.247 g, 1.21 mmol), Boc-alanine (0.24 g, 1.27 mmol), and HOAT (0.165 g, 1.21 mmol) in DCM at 0° C. under nitrogen was added N-(3-dimethylaminopropyl)-n′-ethylcarbodiimide hydrochloride (0.244 g, 1.27 mmol). The reaction was stirred and allowed to warm to RT overnight. The mixture was diluted with DCM (20 mL) and washed with 0.5M NaHCO3 (20 mL). The organic extract was dried (Na2SO4), concentrated in vacuo and purified by column chromatography (Si—PCC, gradient 0-8% (9:1 MeOH/0.880 NH3) in DCM). Product containing fractions were evaporated to give the title compound, (0.272 g, 60%) LCMS (Method J): RT=1.93 min, [M+H]+=376.20

Workup

  1. washwashed with 0.5M NaHCO3 (20 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (Si—PCC, gradient 0-8% (9:1 MeOH/0.880 NH3) in DCM)
  6. additionProduct containing fractions
  7. customwere evaporated

Sources & evidence

ORD record
ord-85f82d22eb5446d689f9fe2cf0bd0685
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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