Imidazole → HCID 71153437, compound

HRID 1497285Notes

Reaction equation

HRID 1497285 reaction equation
[OH:1][C@@H:2]1[C@H:7]2[NH:8][C:9](=[O:11])[O:10][C@H:6]2[CH2:5][C@H:4]([CH2:12][OH:13])[C@H:3]1[OH:14].N1C=CN=C1.[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C=O)C.O>[Si:24]([O:13][CH2:12][C@@H:4]1[C@@H:3]([OH:14])[C@H:2]([OH:1])[C@H:7]2[NH:8][C:9](=[O:11])[O:10][C@H:6]2[CH2:5]1)([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 640418HCID 640418, compound

Product 1

HCID 71153437HCID 71153437, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (3aR,4R,5R,6R,7aS)-4,5-dihydroxy-6-(hydroxymethyl)hexahydrobenzo[d]oxazol-2(3H)-one (2.23 g, 11.0 mmol) in DMF (15 mL) at room temperature was added imidazole (2.24 g, 33.0 mmol) followed by TBDMSCl (1.98 g, 13.2 mmol). The mixture was stirred at this temperature for 2.5 h. The mixture was diluted with water (150 mL) and extracted with EtOAc (5×50 mL). The extracts were dried with MgSO4 and the solvents were evaporated. The crude product was purified by silica gel column chromatography, eluted with 5% MeOH in DCM to give the product (3aR,4R,5R,6R,7aS)-6-(((tert-butyldimethylsilyl)oxy)methyl)-4,5-dihydroxyhexahydrobenzo[d]oxazol-2(3H)-one (2.57 g, 74%) as a white solid. 1H NMR (400 MHz, MeOD) δ 4.68-4.71 (m, 1H), 3.85 (dd, J=8.0 Hz, 3.2 Hz, 1H), 3.63 (dd, J=8.0 Hz, 5.2 Hz, 1H), 3.47-3.55 (m, 2H), 3.37 (t, J=7.8 Hz, 1H), 2.14 (dt, J=12.5 Hz, 2.3 Hz, 1H), 1.86-1.94 (m, 1H), 1.52-1.58 (m, 1H), 0.89 (s, 9H), 0.08 (s, 6H).

Workup

  1. extractionextracted with EtOAc (5×50 mL)
  2. dry with materialThe extracts were dried with MgSO4
  3. customthe solvents were evaporated
  4. customThe crude product was purified by silica gel column chromatography
  5. washeluted with 5% MeOH in DCM

Sources & evidence

ORD record
ord-c383c27ecc2343f499e86c38ba995af8
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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