Methanol → HCID 68292125, compound

HRID 1038372Notes

Reaction equation

HRID 1038372 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-d31977d972964dc380f5bc1865357bf5
Source dataset
uspto-grants-2013_10
Patent number
US08551982B2

Reaction notes

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