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

HRID 1582370

反応式

HRID 1582370 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4c95cb43c66d4c578150478395b167e3
出典データセット
uspto-grants-2004_05
特許番号
US06734200B1

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