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

HRID 1635693노트

반응식

HRID 1635693 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8900Heptane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-95ca39345b9f4dc7b186e1f9207d3715
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509500B2

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