4-Methyloxybenzyl chloride → Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]acetate

HRID 524402Notes

Reaction equation

HRID 524402 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[S:9][CH:10]=1)[CH3:2].C1CCN2C(=NCCC2)CC1.[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Cl)=[CH:35][CH:34]=1>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[N:7]=[C:8]([N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:37][C:36]2[CH:39]=[CH:40][C:33]([O:32][CH3:31])=[CH:34][CH:35]=2)[S:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13240238HCID 13240238, compound

Product 1

HCID 67376904Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]acetateYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-tert-Butoxycarbonylamino-thiazol-4-yl)-acetic acid ethyl ester (7.5 g, 26.11 mmol) in 100 mL of dry dichloromethane was added DBU (11.96 g, 78.56 mmol) followed by para-methoxybenzyl chloride (6.15 g, 39.28 mmol) and the reaction mixture was stirred for 18 hrs at room temperature. The reaction was quenched with water and the layers were separated. The organic layer was washed with brine and dried over anhydrous sodium sulphate and the solvent was removed in vacuo. The residue was purified by column chromatography (silica gel 60-120 mesh and 2-10% ethyl acetate in hexanes as eluent) to get the pure compound (8.0 g).

Workup

  1. customThe reaction was quenched with water
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography (silica gel 60-120 mesh and 2-10% ethyl acetate in hexanes as eluent)

Sources & evidence

ORD record
ord-c3b29fac65f1409591996f72242bcd1e
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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