Trifluoroacetic acid → HCID 178472361, 화합물

HRID 928116노트

반응식

HRID 928116 반응식
[Br:1][C:2]1[S:6][C:5]([C:7]2([C@H:10]3[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]3)[CH2:9][O:8]2)=[N:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([CH:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9][OH:8])=[N:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 178472329HCID 178472329, 화합물

생성물 1

HCID 178472361HCID 178472361, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution in DCM (0.7 mL) of ethyl trans-4-[2-(5-bromo-1,3-thiazol-2-yl)oxiran-2-yl]cyclohexanecarboxylate (30 mg, 0.082 mmol) from Step 2 was treated with trifluoroacetic acid (0.266 mL, 1.665 mmol) and triethylsilane (0.128 mL, 1.665 mmol) and left at 45° C. 16 h. The volatiles were removed under reduced pressure and the residue was taken up in dichloromethane, washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford racemic ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-2-hydroxyethyl]cyclohexanecarboxylate which was used as such without further characterization. MS ESI calc'd. for C14H20BrNO3S [M+H]+ 362, 364, found 362, 364.

후처리

  1. waitleft at 45° C
  2. custom16 h
  3. customThe volatiles were removed under reduced pressure
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-823ca7f188f041e3af218088e6678582
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290490B2

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