Benzyl Bromide → HCID 86701109, compound

HRID 1396257Notes

Reaction equation

HRID 1396257 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:18][C@H:17]2[C@H:13]([N:14]=[C:15]([N:19]([CH2:27][CH2:28][F:29])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[S:16]2)[C@@H:12]([OH:30])[C@@H:11]1[OH:31])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C=O>[CH2:35]([O:31][C@@H:11]1[C@@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[O:18][C@H:17]2[C@H:13]([N:14]=[C:15]([N:19]([CH2:27][CH2:28][F:29])[C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[S:16]2)[C@H:12]1[O:30][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86701107HCID 86701107, compound

Product 1

HCID 86701109HCID 86701109, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl (3aR,5R,6S,7R,7aR)-5-((tert-butyldimethylsilyloxy)methyl)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate (2.0 g, 4.2 mmol) in N,N-dimethylformamide (30 mL) was treated with sodium hydride (510 mg, 21 mmol) for 10 min at 10° C. in a nitrogen atmosphere, and followed by addition of 1-(bromomethyl)benzene (2.2 g, 13 mmol). After stirred for 15 min, the reaction was quenched with saturated aqueous NH4Cl and extracted with dichloromethane (3×30 mL). The organic layers were dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 1.5-3% ethyl acetate in petroleum ether to provide compound 70 as a yellow oil (0.7 g, 25%). (ES, m/z) [M+H]+ 660.8; 1H NMR (300 MHz, CDCl3) δ 7.28-7.43 (m, 10H), 6.11-6.13 (d, J=6.3 Hz, 1H), 4.60-4.74 (m, 4H), 4.30-4.41 (m, 6H), 3.73-3.75 (m, 3H), 3.37-3.44 (m, 1H), 1.54 (s, 9H), 0.90 (s, 9H), 0.06 (s, 6H).

Workup

  1. customthe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with dichloromethane (3×30 mL)
  3. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by a silica gel column
  7. washeluting with 1.5-3% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-ba9d2f95db7f41b8b5bb69f41e2d055c
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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