Hydrochloric Acid → (R(R*,R*))-2-Amino-1-(p-(methylsulphonyl)phenyl)propane-1,3-diol

HRID 1879338노트

반응식

HRID 1879338 반응식
C([O:3][C:4](=O)[C@@H:5]([NH2:18])[C@@H:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[OH:7])C.[BH4-].[K+].Cl.O>CO>[NH2:18][C@H:5]([CH2:4][OH:3])[C@@H:6]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][CH:13]=1)[OH:7]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4192641Potassium borohydrideHCID 34175685(2S,3R)-Ethyl-2-amino-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-propanoate

생성물 1

HCID 6452441(R(R*,R*))-2-Amino-1-(p-(methylsulphonyl)phenyl)propane-1,3-diol

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(2S,3R)-Ethyl-2-amino-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-propanoate (Compound VIc) (10 g, 0.0348 moles) in methanol (about 100 mL) is reacted in a reaction vessel with potassium borohydride (about 2.8 g, 0.0522 moles) over about 6 hours while maintaining the temperature below about 60° C. The reaction is cooled to ambient room temperature and about 1N HCl and water (about 75 mL) are added. Thereafter, the solution is heated to evaporate the methanol. Next, sodium hydroxide is added (about 25%), the resulting solids are filtered and washed with water, then dried to yield (1R,2R)-2-amino-1-[4-(methylsulfonyl)phenyl]-1,3-propanediol (Compound V wherein R1 is methylsulfonyl).

후처리

  1. temperaturewhile maintaining the temperature below about 60° C
  2. temperatureThereafter, the solution is heated
  3. customto evaporate the methanol
  4. additionNext, sodium hydroxide is added (about 25%)
  5. filtrationthe resulting solids are filtered
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-311253c4149e445aa90e865a3291f6be
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314252B2

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