Hydrochloric Acid → N-[[3-(1,3-Dioxolan-2-yl)-2-thienyl]sulfonyl]-N-(4-methoxyphenylmethyl) glycine Ethyl Ester

HRID 1736011Notes

Reaction equation

HRID 1736011 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][NH:6][S:7]([C:10]1[S:11][CH:12]=[CH:13][C:14]=1[CH:15]1[O:19][CH2:18][CH2:17][O:16]1)(=[O:9])=[O:8])[CH3:2].CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Cl)=[CH:36][CH:35]=1.Cl>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]([S:7]([C:10]1[S:11][CH:12]=[CH:13][C:14]=1[CH:15]1[O:16][CH2:17][CH2:18][O:19]1)(=[O:8])=[O:9])[CH2:38][C:37]1[CH:40]=[CH:41][C:34]([O:33][CH3:32])=[CH:35][CH:36]=1)[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 699934-Methyloxybenzyl chlorideHCID 21480494N-[[3-(1,3-dioxolan-2-yl)-2-thienyl]sulfonyl]glycine ethyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 53954663N-[[3-(1,3-Dioxolan-2-yl)-2-thienyl]sulfonyl]-N-(4-methoxyphenylmethyl) glycine Ethyl EsterYield 101.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Example 10, Step A (2.80 g, 8.72 mmol) in anhydrous DMF (40 mL) at 0° C. was added a solution of potassium t-butoxide in t-butanol (1M, 9.16 mL, 9.16 mmol) followed by 4-methoxybenzyl chloride (1.78 g, 11.34 mmol). The solution was stirred at ambient temperature for 4 h, poured into 2N HCl (50 mL), diluted with water (150 mL) and extracted with ethyl acetate (2×120 mL). The combined extracts were dried (MgSO4), filtered and evaporated to give a viscous oil (3.91 g) which was used in the next step.

Workup

  1. extractionextracted with ethyl acetate (2×120 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-32e2a4e5f05841909f6264a9d0e8dbde
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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