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

HRID 1582370Notes

Reaction equation

HRID 1582370 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4c95cb43c66d4c578150478395b167e3
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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