Potassium Carbonate → (S)-Methyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)-phenoxy)methyl)benzoate

HRID 2284838Notes

Reaction equation

HRID 2284838 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:18]([O:17][C:16]([NH:15][C@@H:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)=[O:22])([CH3:19])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 90209372(S)-tert-butyl((3-hydroxyphenyl)(phenyl)methyl)carbamate

Product 1

HCID 86720809(S)-Methyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)-phenoxy)methyl)benzoateYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (S)-tert-butyl ((3-hydroxyphenyl)(phenyl)methyl)carbamate (I8, 3.20 g, 10.7 mmol), methyl 4-(bromomethyl)benzoate (2.70 g, 11.8 mmol) and potassium carbonate (2.20 g, 16.1 mmol) in acetonitrile (54 mL) was stirred at RT for 16 h. The reaction mixture was removed in vacuo and the residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with further ethyl acetate and the combined organic extracts were dried with anhydrous magnesium sulfate, filtered and the solvent was removed in vacuo. The residue was re-crystallised from ethyl acetate and iso-hexane to afford (S)-Methyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)-phenoxy)methyl)benzoate as a white solid (3.25 g, 68%). 1H NMR (400 MHz, CDCl3): δ 8.04 (d, J=8.2 Hz, 2 H), 7.46 (d, J=8.2 Hz, 2 H), 7.34-7.20 (m, 6 H), 6.90-6.81 (m, 3 H), 5.87 (s, 1 H), 5.13 (s, 1 H), 5.07 (s, 2 H), 3.92 (s, 3 H), 1.44 (s, 9 H).

Workup

  1. customThe reaction mixture was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with further ethyl acetate
  4. dry with materialthe combined organic extracts were dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was re-crystallised from ethyl acetate and iso-hexane

Sources & evidence

ORD record
ord-ae1c35542f3c46cc9fc1321fdbd65d71
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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