Dimethylformamide → HCID 60675698, compound

HRID 1257928Notes

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

Reactant 5

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

HCID 3026814-Bromo-2-fluorobenzoic acid

HCID 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

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

Sources & evidence

ORD record: ord-88294207160741a39da5c05d7a3a4c3c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461330B2

Reaction notes

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