Imidazole → HCID 71114747, compound

HRID 1912049Notes

Reaction equation

HRID 1912049 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([CH:16]([CH2:25][CH2:26][OH:27])[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.N1C=CN=C1.[C:38]([Si:42](Cl)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([CH3:41])([CH3:40])[CH3:39]>O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([CH:16]([CH2:25][CH2:26][O:27][Si:42]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 71127320HCID 71127320, compound

Product 1

HCID 71114747HCID 71114747, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-hydroxyvalerate (401 g) and DMF (2000 mL) were mixed. To the mixture were added imidazole (160 g) and tert-butylchlorodiphenylsilane (287 mL) at ice temperature. The mixture was stirred at RT for 1 hr. After pouring water (1.2 L) into the reaction, the mixture was extracted with toluene (2.3 L). The organic layer was washed with aqueous 20 w/v % citric acid (1.6 L), water (2 L) and 10 w/v % brine (1.6 L), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (744.2 g) as a crude product.

Workup

  1. custominto the reaction
  2. extractionthe mixture was extracted with toluene (2.3 L)
  3. washThe organic layer was washed with aqueous 20 w/v % citric acid (1.6 L), water (2 L) and 10 w/v % brine (1.6 L)
  4. dry with materialdried over sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-099328222b424d0d8978ad73a4bf3436
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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