Pivaloyl chloride → HCID 57771391, compound

HRID 2070587Notes

Reaction equation

HRID 2070587 reaction equation
[CH2:1]([O:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH2:22][CH2:21][CH2:20][C:19]3([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:18]=2)=[CH:11][CH:10]=1)[CH2:5][C:6](O)=[O:7])[CH3:2].C(Cl)(=O)C(C)(C)C.[CH2:35]([C@@H:42]1[CH2:46][O:45][C:44](=[O:47])[NH:43]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[Br-].[Li+]>O1CCCC1.C(N(CC)CC)C>[CH2:35]([C@@H:42]1[CH2:46][O:45][C:44](=[O:47])[N:43]1[C:6](=[O:7])[CH2:5][CH:4]([O:3][CH2:1][CH3:2])[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]2[CH2:22][CH2:21][CH2:20][C:19]3([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:18]=2)=[CH:13][CH:14]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 62493Pivaloyl chlorideHCID 82050Lithium BromideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 57771363HCID 57771363, compound

Product 1

HCID 57771391HCID 57771391, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-32.5 °C

Procedure

To a solution of 3-ethoxy-3-[4-(spiro[5.5]undec-1-en-2-ylmethoxy)-phenyl]-pr opionic acid (2.95 g) obtained in Example 41 and triethylamine (3.3 mL) in tetrahydrofuran (60 mL) was added dropwise a solution of pivaloyl chloride (1.265 mL) in tetrahydrofuran (5 mL) at −35° C., followed by stirring the reaction mixture at −35 to −30° C. for 30 minutes. Then, to the reaction mixture was added dropwise a solution of (R)-4-benzyl-2-oxazolidinone (1.82 g) and lithium bromide (892 mg) in tetrahydrofuran (10 mL), followed by raising the temperature up to 0° C. over 2 hours while stirring the reaction mixture. The reaction mixture was poured into ice-cold water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by mid-pressure preparative chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:5) to give (R)-4-benzyl-3-(3-ethoxy-3-[4-(spiro[5.5]undec-1-en-2-ylmethoxy)-phenyl]-propionyl)oxazolidin-2-one.

Workup

  1. temperatureby raising the temperature up to 0° C. over 2 hours
  2. stirringwhile stirring the reaction mixture
  3. additionThe reaction mixture was poured into ice-cold water
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by mid-pressure preparative chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:5)

Sources & evidence

ORD record
ord-9efd1b8befce4d6491ce2cdae1364c44
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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