Sodium bis(trimethylsilyl)amide → HCID 68292731, compound

HRID 529452Notes

Reaction equation

HRID 529452 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([C@@H:14](/[CH:30]=[CH:31]/[CH2:32][C:33]([N:35]1[C@@H:39]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:38][O:37][C:36]1=[O:47])=[O:34])[C:15]([N:17]1[C@@H:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20][O:19][C:18]1=[O:29])=[O:16])[CH:12]=[CH2:13].[CH2:48]([O:55][C:56]1[CH:61]=[CH:60][C:59]([CH2:62]Br)=[CH:58][CH:57]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C1COCC1>[CH2:11]([C@@H:14](/[CH:30]=[CH:31]/[C@H:32]([CH2:62][C:59]1[CH:60]=[CH:61][C:56]([O:55][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[CH:57][CH:58]=1)[C:33]([N:35]1[C@@H:39]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:38][O:37][C:36]1=[O:47])=[O:34])[C:15]([N:17]1[C@@H:21]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:20][O:19][C:18]1=[O:29])=[O:16])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 104927561-(Benzyloxy)-4-(bromomethyl)benzeneHCID 68292373HCID 68292373, compound

Product 1

HCID 68292731HCID 68292731, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of NaHMDS (1.0 M in THF, 0.258 mL, 0.258 mmol) was added dropwise to a −78° C. solution of (S,E)-2-allyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)hex-3-ene-1,6-dione (118 mg, 0.235 mmol) in THF (1.0 mL). After stirring at −78° C. for 40 min, a solution of 1-(benzyloxy)-4-(bromomethyl)benzene (78 mg, 0.282 mmol) in THF (0.2 mL) was added dropwise. The reaction temperature was then slowly raised to 0° C. over 45 min. After 30 min at 0° C., the reaction temperature was allowed to reach rt. After 2 h at rt, the reaction mixture was quenched by addition of saturated NH4Cl. The mixture was partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4 and concentrated. The crude product was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give (2S,5S,E)-2-allyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-(4-(benzyloxy)benzyl)hex-3-ene-1,6-dione (47 mg, 0.067 mmol, 29%) as a white solid. Anal. Calcd. for C43H42N2O7 m/z 698.2. found: 699.2 (M+H)+.

Workup

  1. temperatureThe reaction temperature was then slowly raised to 0° C. over 45 min
  2. waitAfter 30 min at 0° C.
  3. customto reach rt
  4. waitAfter 2 h at rt
  5. customthe reaction mixture was quenched by addition of saturated NH4Cl
  6. customThe mixture was partitioned between EtOAc and water
  7. customThe organic phase was isolated
  8. washwashed with saturated aqueous NaCl
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. customThe crude product was purified
  12. washeluting with a gradient of 0-100% EtOAc/Hex

Sources & evidence

ORD record
ord-85c7252d8e144447a69a6685b92b4ca6
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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