Hydrochloric Acid → tert-Butyl (3S)-3-[((3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-ylamino)-carbonyl]piperidine-1-carboxylate

HRID 656345노트

반응식

HRID 656345 반응식
[Cl:1][C:2]1[C:3]([CH3:25])=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18](=[O:24])OC(C)(C)C)[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[C:61]([O:65][C:66]([N:68]1[CH2:73][CH2:72][CH2:71][C@H:70](C(O)=O)[CH2:69]1)=[O:67])([CH3:64])([CH3:63])[CH3:62]>O1CCOCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([CH3:25])=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18]([C@H:72]3[CH2:71][CH2:70][CH2:69][N:68]([C:66]([O:65][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:67])[CH2:73]3)=[O:24])[CH2:12]2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6951168(3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 86602353tert-butyl {(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}carbamate

생성물 1

HCID 58656262tert-Butyl (3S)-3-[((3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-ylamino)-carbonyl]piperidine-1-carboxylate

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

tert-Butyl {(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}carbamate (58.34 mg, 0.0001500 mol) was treated with 4.0 M of hydrogen chloride in 1,4-dioxane (1.0 mL) at rt for 30 min. The solvent was evaporated under reduced pressure and the residue was dissolved in DMF (1.0 mL) and to this was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (69.6 mg, 0.000157 mol), 4-methylmorpholine (100.0 uL, 0.0009096 mol), and (3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (34.4 mg, 0.000150 mol) at rt. After stirring for 1 h, the reaction mixture was diluted with ethyl acetate (5 mL) and washed with NaHCO3 (7.5%, 3×2 mL) and brine (3×20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product which was used directly in the next step without further purification.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (1.0 mL)
  3. washwashed with NaHCO3 (7.5%, 3×2 mL) and brine (3×20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5f08e6ab20984ba0a70355ba0ce30c6e
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071624B2

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