Hydrochloric Acid → Sodium difluorosulfoacetate

Under cooling with an ice bath, 230 parts of a 30 mass % aqueous sodium hydroxide solution was dripped into a mixture of 100 parts of methyl difluoro(fluorosulfonyl)acetate and 150 parts of ion-exchanged water. The resultant mixture was refluxed at 100° C. for three hours, was cooled, and was neutralized with 88 parts of concentrated hydrochloric acid. The obtained solution was concentrated to obtain 164.4 parts of sodium difluorosulfoacetate (which contains an inorganic salt, and the purity is 62.7%). To a mixture of 1.9 parts of the sodium difluorosulfoacetate (the purity is 62.7%) obtained and 9.5 parts of N,N-dimethylformamide, 1.0 part of 1,1′-carbonyldiimidazole was added, and the resultant mixture was stirred for two hours. The obtained solution was added to a solution which was obtained by adding 0.2 parts of sodium hydride to a mixture of 1.1 parts of 3-hydroxy-1-adamantylmethanol and 5.5 parts of N,N-dimethylformamide, and stirring the resultant mixture for two hours. The resultant solution was stirred for 15 hours to obtain sodium salt of 3-hydroxy-1-adamantylmethyl difluorosulfoacetate, which was used as it was for the subsequent reaction.

1. temperatureUnder cooling with an ice bath
2. temperaturewas cooled
3. concentrationThe obtained solution was concentrated

ORD record

ord-7883214a0e5247a9bc6fe088da4f52d6

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916330B2