Methanol → HCID 68292125, compound

HRID 2276924Notes

Reaction equation

HRID 2276924 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]3[O:26][C:25]4[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=4[O:23][CH2:22]3)=[CH:17][CH:16]=2)[CH2:12][CH3:13])=[CH:6][CH:5]=1.O[Li].O.CO.O>C(O)(=O)C>[O:26]1[C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[O:23][CH2:22][C@@H:21]1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=2)[CH2:12][CH3:13])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68292763HCID 68292763, compound

Product 1

HCID 68292125HCID 68292125, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-({[(S)-4-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-ethyl-amino}-methyl)-benzoic acid methyl ester (65 mg, 0.16 mmol), LiOH.H2O (23 mg, 0.55 mmol), MeOH (5 mL) and water (0.5 mL) is stirred at room temperature for 16 h. The reaction mixture is neutralized with acetic acid and concentrated. The residue is diluted with water and DCM, phases are separated, the organic layer is dried over Na2SO4, filtered and concentrated. The residue is purified by flash chromatography eluting with a gradient of 0-10% MeOH in DCM to give the title compound.

Workup

  1. concentrationconcentrated
  2. additionThe residue is diluted with water and DCM, phases
  3. customare separated
  4. dry with materialthe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography
  8. washeluting with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-7f2cfcb3c4da4f21ba5dc71cffdbc988
Source dataset
uspto-grants-2015_09
Patent number
US09133146B2

Reaction notes

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