Water → [4-(2-Methoxy-ethoxymethyl)-thiazol-2-yl]-carbamic acid phenyl ester

HRID 1020249Notes

Reaction equation

HRID 1020249 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[N:12]=1)([CH3:4])([CH3:3])C.ClC(O[C:24]1[CH:29]=CC=C[CH:25]=1)=O.O>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C1COCC1>[C:1]1([O:5][C:6](=[O:19])[NH:7][C:8]2[S:9][CH:10]=[C:11]([CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[N:12]=2)[CH:3]=[CH:29][CH:24]=[CH:25][CH:4]=1

Participants

7

Reactant 3

HCID 962WaterHCID 15891Phenyl chloroformateHCID 86622744tert-Butyl-4-((2-methoxyethoxy)methyl)thiazol-2-ylcarbamate2×

Product 1

HCID 86622750[4-(2-Methoxy-ethoxymethyl)-thiazol-2-yl]-carbamic acid phenyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-butyl 4-((2-methoxyethoxy)methyl)thiazol-2-ylcarbamate (Intermediate III, 3.4 g, 0.018 mol) was dissolved in pyridine (50 mL) and a catalytic amount of DMAP was added (0.2 g, ˜10 mol %). To this mixture a solution of phenyl chloroformate (2.27 mL, 1 eq.) in THF (50 mL) was added drop wise and the resulting reaction mixture was stirred for 3 hours at ambient temperature. Then, H2O was added and the diluted mixture was extracted with EtOAc. Dried the organic layer over Na2SO4, filtered and concentrated in vacuo. Purification over SiO2 eluting with 1:1 EtOAc/heptane gave 2.4 gram of the product as a yellow fluffy solid. 1H-NMR (300 MHz, DMSO-d6) δ 11.70 (s, br, 1H), 7.42 (d, 1H), 7.37 (m, 1H), 7.08 (m, 3H), 4.59 (s, 2H), 4.38 (d, 2H), 3.30 (s, 2H), 3.23 (t, 2H), 1.75 (q, 2H), 0.97 (t, 3H).

Workup

  1. customthe resulting reaction mixture
  2. extractionthe diluted mixture was extracted with EtOAc
  3. dry with materialDried the organic layer over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification over SiO2 eluting with 1:1 EtOAc/heptane

Sources & evidence

ORD record
ord-b2ab6948020b47f9b5f6f3554a393e60
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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