4-Ethylphenyl isocyanate → HCID 59778441, compound

HRID 655964Notes

Reaction equation

HRID 655964 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH2:39]([C:41]1[CH:46]=[CH:45][C:44]([N:47]=[C:48]=[O:49])=[CH:43][CH:42]=1)[CH3:40]>C1COCC1.CN(C1C=CN=CC=1)C>[CH2:39]([C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:48](=[O:49])[O:8][CH2:9][C@@H:10]([N:12]([CH3:20])[C:13]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:19])[CH3:11])=[CH:43][CH:42]=1)[CH3:40]

Participants

6

Reactant 3

HCID 900074-Ethylphenyl isocyanateHCID 2724141Tetrabutylammonium FluorideHCID 59778587HCID 59778587, compound

Product 1

HCID 59778441HCID 59778441, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)propan-2-yl(methyl)carbamate (301 mg, 1.0 mmol) in THF was added TBAF (1M in THF, 1.5 mL, 1.5 mmol, 1.5 equiv.) and the mixture was stirred for 1 h followed by quenched with saturated NaHCO3 and diluted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to give a crude oil, which was re-dissolved in THF (2.0 mL). To this THF solution were added DMAP and 4-ethylphenyl isocyanate. The reaction mixture was stirred for 30 min. LC/MS indicated the completion of the reaction and the mixture was filtered and the filtrate was purified on RP-HPLC using a mixture of acetonitrile and H2O to give (S)-2-(methyl(tert-butoxycarbonyl)amino)propyl 4-ethylphenylcarbamate (118 mg, 30% from 1). LRMS (M-Boc+H+) m/z 237.1.

Workup

  1. customby quenched with saturated NaHCO3
  2. additiondiluted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give a crude oil, which
  9. stirringThe reaction mixture was stirred for 30 min
  10. customthe completion of the reaction
  11. filtrationthe mixture was filtered
  12. customthe filtrate was purified on RP-HPLC
  13. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-f5bdffbc07124dafbfaff0f8f251c07c
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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