Dimethylformamide → HCID 60675698, compound

HRID 500276Notes

Reaction equation

HRID 500276 reaction equation
C(N(CC)C(C)C)(C)C.Cl.[NH2:11][CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14].[Br:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([F:28])[CH:20]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O>>[Br:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:11][CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14])=[O:24])=[C:21]([F:28])[CH:20]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3026814-Bromo-2-fluorobenzoic acidHCID 2756298Alanine, methyl ester, hydrochloride (1:1)

Product 1

HCID 60675698HCID 60675698, compoundYield 96%

Procedure

N,N-Diisopropylethylamine (2.0 mL, 0.011 mol) was added to a mixture of methyl 2-aminopropanoate hydrochloride (0.64 g, 0.0046 mol), 4-bromo-2-fluorobenzoic acid (1.0 g, 0.0046 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.12 g, 0.00479 mol) in N,N-dimethylformamide (10.0 mL, 0.129 mol). The reaction mixture was stirred overnight at RT, quenched with saturated sodium bicarbonate (25 mL) and extracted with EtOAc (3×40 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel with 60% EtOAc in hexanes to afford the desired product (1.33 g, 96%). LCMS: (M+H)=303.9/305.9.

Workup

  1. customquenched with saturated sodium bicarbonate (25 mL)
  2. extractionextracted with EtOAc (3×40 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel with 60% EtOAc in hexanes

Sources & evidence

ORD record
ord-3e12405b64804024acf2dec9c0f35325
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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