Methylamine → HCID 67223969, compound

HRID 1257911Notes

Reaction equation

HRID 1257911 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:21])[C:18](O)=[O:19])=[C:13]([F:22])[CH:12]=1.CN.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:21])[C:18]([NH:4][CH3:1])=[O:19])=[C:13]([F:22])[CH:12]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27569814-Bromo-2-fluoromandelic acid

Product 1

HCID 67223969HCID 67223969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (0.2 mL, 0.001 mol) was added to a mixture of (4-bromo-2-fluorophenyl)(hydroxy)acetic acid (0.1 g, 0.4 mmol), methylamine (2M in THF, 0.24 mL, 0.48 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.21 g, 0.00048 mol) in methylene chloride (2 mL). The mixture was stirred at RT for 2 h. The reaction mixture was concentrated. The residue was purified by chromatography on silica gel with 10% methanol in dichloromethane to afford the desired product. LCMS: (M+H)=261.9/263.9.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was purified by chromatography on silica gel with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-1c01b7f66593416b83e60333c0237f36
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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