Benzyl Bromide → HCID 141206097, compound

HRID 1502633Notes

Reaction equation

HRID 1502633 reaction equation
[H-].[Na+].O[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[NH:12].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1C[O:39]CC1>>[CH2:28]([O:39][CH:8]([CH2:7][CH2:6][CH2:5][CH3:4])[CH2:9][N:10]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[NH:12])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 7498Benzyl Bromide2×HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydride4×HCID 141206098HCID 141206098, compound

Product 1

HCID 141206097HCID 141206097, compoundYield 34%

Procedure

1.300 g (32.49 mmol, 1.3 eq.) of sodium hydride were suspended under nitrogen in 170 mL of dry THF. 8.983 g (24.99 mmol, 1 eq.) of 1-(6-hydroxyhexyl)-N,N′-di-Boc-guanidine dissolved in dry THF were added dropwise to the suspension. The reaction was stirred at room temperature for 45min. 3.6 mL (29.99 mmol, 1.2 eq.) of benzyl bromide were added dropwise in 10min. The reaction was stirred overnight at room temperature. The reaction was checked by TLC and the reaction wasn't complete. 0.833 g (20.82 mmol) of sodium hydride were added. After 1 hour, the TLC was the same and 0.810 g (20.24 mmol) of sodium hydride were added. After 3 hours, no evolution was seen on TLC, 1.396 g (34.89 mmol) of sodium hydride and 1.6 mL (13.33 mmol) of benzyl bromide were added. The reaction was stirred overnight and TLC was still the same. The reaction was quenched by addition of water until clear solution. THF was removed in vacuo. Aqueous phase was extracted 3 times with ether. Organic phase was dried over anhydrous Na2SO4 and evaporated to obtain 15.44 g of a slightly yellow oil. This oil was purified by flash chromatography over silica (eluant AcOEt:pentane 1:9; Rf=0.43) to obtain 3.78 g of 1-(2-(benzyloxy)hexyl)-N,N′-di-Boc-guanidine as a colorless oil (yield=34%). 1H-NMR (500 MHz, CDCl3): δ=1.39 (m, 5H), 1.50 (s, 9H), 1.51 (s, 9H), 1.61 (m, 5H), 3.45 (m, 4H), 4.50 (m, 2H), 7.28 (m, 1H), 7.34 (m, 4H).

Workup

  1. additionwere added dropwise to the suspension
  2. stirringThe reaction was stirred overnight at room temperature
  3. waitAfter 1 hour
  4. additionwere added
  5. waitAfter 3 hours
  6. additionwere added
  7. stirringThe reaction was stirred overnight
  8. customThe reaction was quenched by addition of water until clear solution
  9. customTHF was removed in vacuo
  10. extractionAqueous phase was extracted 3 times with ether
  11. dry with materialOrganic phase was dried over anhydrous Na2SO4
  12. customevaporated
  13. customto obtain 15.44 g of a slightly yellow oil
  14. customThis oil was purified by flash chromatography over silica (eluant AcOEt:pentane 1:9; Rf=0.43)

Sources & evidence

ORD record
ord-77d74729aca34988826b8ddb3ae8ee11
Source dataset
uspto-grants-2015_12
Patent number
US09211340B2

Reaction notes

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