Phosphoric Acid → Tetradecanoic acid, 2-[4-[(butylsulfonyl)amino]phenoxy]-, methyl ester

HRID 1635693Notes

Reaction equation

HRID 1635693 reaction equation
P([O-])([O-])([O-])=O.[OH-].[K+].P(=O)(O)(O)O.[NH2:13][C:14]1[CH:37]=[CH:36][C:17]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1.[CH2:38]([S:42](Cl)(=[O:44])=[O:43])[CH2:39][CH2:40][CH3:41]>CCCCCCC.O>[CH2:38]([S:42]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:20]([O:22][CH3:23])=[O:21])=[CH:36][CH:37]=1)(=[O:44])=[O:43])[CH2:39][CH2:40][CH3:41]

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 1061PhosphateHCID 14797Potassium HydroxideHCID 754301-Butanesulfonyl chlorideHCID 112569Tetradecanoic acid, 2-(4-aminophenoxy)-, methyl ester

Product 1

HCID 18676574Tetradecanoic acid, 2-[4-[(butylsulfonyl)amino]phenoxy]-, methyl esterYield 91.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8900HeptaneSolvent

Procedure

A phosphate buffer solution composed of 49 g of water, 66 g of 45% aqueous potassium hydroxide (0.53 moles) and 38 g (0.32 moles) of 85% phosphoric acid was treated at room temperature with a solution of 69 g (0.197 moles) of methyl 2-[4-aminophenoxy]tetradecanoate (the amine) in 172 g of heptane. The temperature was adjusted to 30° C. and 37.1 g (0.237 moles) of butanesulfonyl chloride was added dropwise over 1 hr. The two-phase mixture was stirred for 4 hr while the temperature was maintained at 30° C. to 35° C. The product assayed 96.9% on a solvent-free basis. The bottom water layer was removed, and the upper layer was washed several times with 100 mL of water and was crystallized by cooling to ice temperature. The product was filtered and washed with 200 mL of cold heptane to afford 85 g (90% yield) of white solid, 98.9% assay by HPLC.

Workup

  1. customwas adjusted to 30° C.
  2. temperaturewas maintained at 30° C. to 35° C
  3. customThe bottom water layer was removed
  4. washthe upper layer was washed several times with 100 mL of water
  5. customwas crystallized
  6. temperatureby cooling to ice temperature
  7. filtrationThe product was filtered
  8. washwashed with 200 mL of cold heptane

Sources & evidence

ORD record
ord-95ca39345b9f4dc7b186e1f9207d3715
Source dataset
uspto-grants-2003_01
Patent number
US06509500B2

Reaction notes

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