Hydrochloric Acid → HCID 59443764, compound

HRID 1776524Notes

Reaction equation

HRID 1776524 reaction equation
C(OC([N:8]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[O:23][CH2:24][CH:25]1[CH2:27][CH2:26]1)[S:9]([CH3:12])(=[O:11])=[O:10])=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[CH:25]1([CH2:24][O:23][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:13]=2[NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:17]([O:19][CH3:20])=[O:18])[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59443767HCID 59443767, compound

Product 1

HCID 59443764HCID 59443764, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoate (for reference procedure see Example 18, WO 2010/089107, which is incorporated herein by reference) (3.00 g, 7.51 mmol) in dry DCM (40 ml), HCl 4M in Dioxane (9.39 ml, 37.6 mmol) was added, and the mixture was stirred at RT for 3 days. The solvent was evaporated, the residue was triturated with iPr2O (50 ml) and filtered to give methyl 3-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoate as an off-white powder (2.15 g, 7.18 mmol, 96% yield, MS/ESI+ 299.9 [MH]+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with iPr2O (50 ml)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-6de8e336b2c44bb3a33d44674341c050
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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