Triethylamine → (S)-4-Benzyl-3-((2S,3R)-3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-2-ethoxy-3-hydroxy-propionyl)-oxazolidin-2-one

HRID 2215194Notes

Reaction equation

HRID 2215194 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.C(N(CC)CC)C.B(OS(C(F)(F)F)(=O)=O)(CCCC)CCCC.[C:44]([C:48]1[O:49][C:50]([CH3:68])=[C:51]([CH2:53][CH2:54][O:55][C:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[C:59]([CH:66]=[O:67])=[CH:58][CH:57]=2)[N:52]=1)([CH3:47])([CH3:46])[CH3:45]>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[C@@H:15]([O:16][CH2:17][CH3:18])[C@@H:66]([C:59]1[C:60]2[C:65](=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:56]([O:55][CH2:54][CH2:53][C:51]2[N:52]=[C:48]([C:44]([CH3:47])([CH3:46])[CH3:45])[O:49][C:50]=2[CH3:68])=[CH:57][CH:58]=1)[OH:67])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724243Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dibutylborinic acidHCID 10825429(S)-4-Benzyl-3-(ethoxyacetyl)oxazolidin-2-oneHCID 116457474-[2-(2-tert-Butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalene-1-carbaldehyde

Product 1

HCID 11563395(S)-4-Benzyl-3-((2S,3R)-3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-2-ethoxy-3-hydroxy-propionyl)-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

0.234 g of (S)-4-benzyl-3-ethoxyacetyl-oxazolidin-2-one (0.889 mmol) was dissolved under an argon atmosphere in 3 ml of abs. CH2Cl2 and treated with 0.149 ml of triethylamine (1.2 eq.). After cooling to −78°, nBu2BOTf was added slowly (0.980 ml of 1M solution in CH2Cl2) and enolborinate formation allowed to proceed for 15 Min. at −78° and for 50 Min. at 0°. After recooling, a solution of 0.300 g of the above prepared 4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalene-1-carbaldehyde (0.889 mmol) in 5 ml of abs. CH2Cl2 was slowly added via dropping funnel and the mixture kept for 30 Min. at −78° and for additional 30 Min. at 0°. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=1/1) left finally 0.268 g of the title compound as white foam.

Workup

  1. temperatureAfter cooling to −78°
  2. customat −78°
  3. customat 0°
  4. customat −78°
  5. customat 0°
  6. additionPouring
  7. extractionice/NH4Cl, twofold extraction with AcOEt
  8. washwashing with water
  9. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  10. waitleft finally 0.268 g of the title compound as white foam

Sources & evidence

ORD record
ord-d240411705384db7aac8b35310fb7752
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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