Water → HCID 59909738, compound

HRID 2183076Notes

Reaction equation

HRID 2183076 reaction equation
[Br-].[CH:2]1([CH2:6][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:5][CH2:4][CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:36][N:37]([CH3:57])[C:38]([C:40]1[N:41]=[C:42]([C@H:45]([CH2:54][CH:55]=O)[CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[O:43][CH:44]=1)=[O:39].O>O1CCCC1.C1(C)C=CC=CC=1>[CH:2]1(/[CH:6]=[CH:55]\[CH2:54][C@@H:45]([C:42]2[O:43][CH:44]=[C:40]([C:38]([N:37]([CH3:57])[CH3:36])=[O:39])[N:41]=2)[CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 2724254Sodium bis(trimethylsilyl)amideHCID 59909833HCID 59909833, compoundHCID 86583711HCID 86583711, compound

Product 1

HCID 59909738HCID 59909738, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of (cyclobutylmethyl)(triphenyl)phosphonium bromide (Preparation 122) (680 mg, 1.65 mmol) in anhydrous tetrahydrofuran (13 ml), under a nitrogen atmosphere, at 0° C., was treated with sodium bis(trimethylsilyl)amide 1M in tetrahydrofuran (1.65 ml, 1.65 mmol) over a period of 5 minutes. The bright orange mixture was stirred at 0° C. for 1 hour. A solution of tert-butyl (3R)-3-{4-[(dimethylamino)carbonyl]-1,3-oxazol-2-yl}-5-oxopentanoate (Preparation 118) (428 mg, 1.38 mmol) in toluene (4 ml) was added to the mixture and stirred at 0° C. for 30 minutes and allowed to warm to room temperature for a further 30 minutes. Water (2 ml) was added and the solvents were removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with dilute aqueous of potassium sodium tartrate solution and brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure. The oil was purified by column chromatography on silica gel eluting with a solvent gradient of 9:1 (hexane:ethyl acetate) gradually changing to 1:1 (hexane:ethyl acetate) to afford the title compound as a colourless oil (282 mg).

Workup

  1. stirringstirred at 0° C. for 30 minutes
  2. temperatureto warm to room temperature for a further 30 minutes
  3. customthe solvents were removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with dilute aqueous of potassium sodium tartrate solution and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customThe oil was purified by column chromatography on silica gel eluting with a solvent gradient of 9:1 (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-9112b72b0c374ba0871e29cb04dafd86
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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