Triethylamine → HCID 10627061, compound

HRID 1464813Notes

Reaction equation

HRID 1464813 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH2:15][O:16][CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]S(C(F)(F)F)(=O)=O.C([B+]CCCC)CCC.C(N(CC)CC)C.[CH3:44][C:45]1[O:49][C:48]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[N:47][C:46]=1[CH2:56][C:57]1[O:58][C:59]2[CH:65]=[CH:64][C:63]([CH:66]=[O:67])=[CH:62][C:60]=2[CH:61]=1>ClCCl>[OH:67][C@H:66]([C:63]1[CH:64]=[CH:65][C:59]2[O:58][C:57]([CH2:56][C:46]3[N:47]=[C:48]([C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)[O:49][C:45]=3[CH3:44])=[CH:61][C:60]=2[CH:62]=1)[C@H:15]([O:16][CH2:17][CH3:18])[C:14]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 106154122-(5-Methyl-2-phenyl-4-oxazolyl)methyl-5-benzofurancarboxaldehydeHCID 10825429(S)-4-Benzyl-3-(ethoxyacetyl)oxazolidin-2-oneHCID 178418657HCID 178418657, compound

Product 1

HCID 10627061HCID 10627061, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (S)-4-benzyl-3-(ethoxyacetyl)oxazolidin-2-one (1.0 g, 3.8 mmol) in dichloromethane (10 ml), cooled to 0° C., was added freshly distilled dibutylboron triflate (1.1 ml, 4.6 mmol) dropwise, followed by triethylamine (0.69 m), 4.9 mmol). After 5 minutes the solution was cooled to -78° C. and a precooled solution of 2-(5-methyl-2-phenyl-4-oxazolyl) methyl-5-benzofurancarboxaldehyde (1.33 g, 4.2 mmol) in dichloromethane (5 ml) was added. After 20 minutes the mixture was warmed to 0° C. and stirred at that temperature for 1 hour then quenched with a solution of pH 7 buffer (10 ml) in methanol (30 ml), followed by a solution of 30% hydrogen peroxide (10 ml) in methanol (30 ml), and stirred at 0° C. for 1 hour. The mixture was then diluted with water and extracted with ethyl acetate (3×). The combined extracts were washed with brine, dried over sodium sulfate and concentrated. The product was purified by flash chromatography (hexanes/ethyl acetate, 1:1) and obtained as a yellow solid (1.16 g, m.p. 66° C.).

Workup

  1. temperatureAfter 20 minutes the mixture was warmed to 0° C.
  2. customthen quenched with a solution of pH 7 buffer (10 ml) in methanol (30 ml)
  3. stirringstirred at 0° C. for 1 hour
  4. additionThe mixture was then diluted with water
  5. extractionextracted with ethyl acetate (3×)
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography (hexanes/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-340cc2b66b744e5dad111d2a79914869
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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