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

HRID 2065472노트

반응식

HRID 2065472 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-a550b4fdc9944c908cf4b53ce86a0faf
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288417B2

반응 노트

불러오는 중…