Tributylphosphine → 5(S)-(Isoxazol-3-yl-aminomethyl)-3-(4-morpholinophenyl)-oxazolidin-2-one

HRID 1582370

반응식

HRID 1582370 반응식
OC[C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH2:4]1.C(OC(N[C:29]1[CH:33]=[CH:32][O:31][N:30]=1)=O)(C)(C)C.C(P(CCCC)CCCC)CCC.[N:47]([C:57](N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[O:31]1[CH:32]=[CH:33][C:29]([CH:57]([NH2:47])[C@H:3]2[O:7][C:6](=[O:8])[N:5]([C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)=[CH:11][CH:10]=3)[CH2:4]2)=[N:30]1

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 20725693(R)-5-(hydroxymethyl)-3-(4-morpholinophenyl)oxazolidin-2-oneHCID 21992950tert-Butyl 1,2-oxazol-3-ylcarbamate

생성물 1

HCID 698904955(S)-(Isoxazol-3-yl-aminomethyl)-3-(4-morpholinophenyl)-oxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5(R)-Hydroxymethyl-3-(4-morpholinophenyl)oxazolidin-2-one (prepared by analogy to the 3-fluoro compound—see WO95/07271; 0.50 g, 1.80 mmol), 3-t-butyloxycarbonylamino-isoxazole (0.50 g, 2.70 mmol), tri-n-butylphosphine (0.66 ml, 2.70 mmol), and 1,1′-(azodicarbonyl)-di-piperidine (0.68 g, 2.70 mmol) were reacted in anhydrous THF (30 ml) using the general method of Reference Example 15. The reaction was then purified by MPLC (Merck 9385 silica, 70% ethyl acetate in iso-hexane) and the solvent removed under reduced pressure to give a solid which was triturated with ether to give the title compound as an off-white solid. 1H-NMR (300 MHz, DMSO-d6): δ=1.50 (s, 9H), 3.08 (t, 4H), 3.70-3.80 (m, 5H), 3.93-4.01 (m, 1H), 4.14-4.30 (m, 2H), 4.95 (m, 1H), 6.88 (s, 1H), 6.99 (d, 2H), 7.40 (d, 2H), 8.81 (s, 1H). MS: ESP+ (M+H)+=445.

후처리

  1. customThe reaction was then purified by MPLC (Merck 9385 silica, 70% ethyl acetate in iso-hexane)
  2. customthe solvent removed under reduced pressure
  3. customto give a solid which
  4. customwas triturated with ether

출처 및 근거

ORD 기록
ord-4c95cb43c66d4c578150478395b167e3
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734200B1

연결된 노트

불러오는 중…