Hydrochloric Acid → (3S)-1-Acetyl-N-{(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}piperidine-3-carboxamide

HRID 2065473노트

반응식

HRID 2065473 반응식
[Cl:1][C:2]1[C:3]([CH3:33])=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][N:22]([C:26](OC(C)(C)C)=[O:27])[CH2:21]3)=[O:19])[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl.[C:35](O)(C(F)(F)F)=O>O1CCOCC1.CO>[C:26]([N:22]1[CH2:23][CH2:24][CH2:25][C@H:20]([C:18]([NH:17][C@H:13]2[CH2:14][CH2:15][CH2:16][N:11]([S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[CH3:33])(=[O:9])=[O:10])[CH2:12]2)=[O:19])[CH2:21]1)(=[O:27])[CH3:35]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 58656262tert-Butyl (3S)-3-[((3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-ylamino)-carbonyl]piperidine-1-carboxylate

생성물 1

HCID 11554020(3S)-1-Acetyl-N-{(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}piperidine-3-carboxamide

시약·촉매·용매 2

HCID 887Methanol용매HCID 312751,4-Dioxane용매

실험 절차

tert-Butyl (3S)-3-[((3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-ylamino)-carbonyl]piperidine-1-carboxylate (10.0 mg, 200 μmol) was treated with 4.0 M of hydrogen chloride in 1,4-dioxane (0.5 mL) at rt for 1 h. The volatiles were removed in-vacuo and the residue was dissolved in acetonitrile (0.8 mL) and was treated with diisopropylethylamine (20.0 μL) and acetyl chloride (5.0 μL). The crude reaction mixture was diluted with MeOH (1.3 mL) and was adjusted to a pH of 2 using TFA and was purified by prep-HPLC to give the desired product. LCMS: (M+H)+=442.1/444.1.

후처리

  1. customThe volatiles were removed in-vacuo
  2. dissolutionthe residue was dissolved in acetonitrile (0.8 mL)
  3. additionwas treated with diisopropylethylamine (20.0 μL) and acetyl chloride (5.0 μL)
  4. customThe crude reaction mixture
  5. customwas purified by prep-HPLC

출처 및 근거

ORD 기록
ord-4f96f53b586a42b2808eea07cc6e9a6e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288417B2

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