Methylamine → HCID 67148438, compound

HRID 2428143Notes

Reaction equation

HRID 2428143 reaction equation
CN.[CH3:3][N:4](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34](O)=[O:35])=[CH:28][C:27]=1[CH2:37][OH:38]>C(Cl)Cl>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([NH:4][CH3:3])=[O:35])=[CH:28][C:27]=1[CH2:37][OH:38]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67148305HCID 67148305, compound

Product 1

HCID 67148438HCID 67148438, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

MeNH2 (2M in THF, 28.0 mL, 56.1 mmol) and TBTU (1.98 g, 6.17 mmol) were added to a sol. of 3-(4-chloro-3-hydroxymethyl-phenyl)-propionic acid (1.20 g, 5.59 mmol) in CH2Cl2 (42 mL). The mixture was stirred at rt for 2.5 h, and CH2Cl2 (150 mL) was added. The mixture was washed with brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (MeOH/CH2Cl2 1:9) yielded the title compound (250 mg, 20%). LC-MS: tR=0.67 min; ES+: 269.34.

Workup

  1. washThe mixture was washed with brine
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (MeOH/CH2Cl2 1:9)

Sources & evidence

ORD record
ord-75d2113c87a34288a88053c398a89f6e
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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