Ethanol → 2-(2-t-Butoxycarbonylaminoethoxy)-4-methylsulfonylbenzoic acid

HRID 1434832Notes

Reaction equation

HRID 1434832 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:19]=[CH:18][C:13]=1[C:14]([O:16]C)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCO.[OH-].[K+]>O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:19]=[CH:18][C:13]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 57936591Methyl 2-(2-t-butoxycarbonylaminoethoxy)-4-methylsulfonylbenzoate

Product 1

HCID 579366282-(2-t-Butoxycarbonylaminoethoxy)-4-methylsulfonylbenzoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 2-(2-t-butoxycarbonylaminoethoxy)-4-methylsulfonylbenzoate (8.6 g, 23 mmol), EtOH (200 mL), and KOH (6.5 g, 115 mmol) in water (200 mL) was heated to 70° C. for 4 hours. The EtOH was removed in vacuo and the residue was diluted with CH2Cl2. The mixture was acidified with satd citric acid and partitioned. The organic layer was dried (Na2SO4) and concentrated to give the desired product as a solid (7.5 g, 91%).

Workup

  1. customThe EtOH was removed in vacuo
  2. additionthe residue was diluted with CH2Cl2
  3. custompartitioned
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e6fb5d921bbf4bc28182b548880eb9fa
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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