Ethyl Acetate → [1-Formyl-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 852860Notes

Reaction equation

HRID 852860 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:46])[NH:13][CH:14]([C:40](=[O:45])N(OC)C)[CH2:15][C:16]1[N:17]=[CH:18][N:19]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=1)([CH3:10])([CH3:9])[CH3:8].CC(=O)OCC.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[C:7]([O:11][C:12](=[O:46])[NH:13][CH:14]([CH:40]=[O:45])[CH2:15][C:16]1[N:17]=[CH:18][N:19]([C:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:20]=1)([CH3:8])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 86591138[1-(Methoxy-methyl-carbamoyl)-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 86591139[1-Formyl-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl esterYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of lithium aluminum hydride (263 mg, 6.92 mmol) in THF (20 mL) was added slowly to [1-(methoxy-methyl-carbamoyl)-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (3.4 g, 6.3 mmol) in THF (75 mL) at −20° C. The reaction was complete (silica gel, EA, Rf 0.48) in 15 minutes. Saturated sodium potassium tartrate (10 mL) was added, and the solvent removed. Water was added and the residue extracted with Et2O. The Et2O was washed with brine, dried and filtered. Removal of the solvent gave the title compound (2.552 g, 84%). ESMS 482 (M+H+) 1H NMR ( ) 13C NMR ( )

Workup

  1. customin 15 minutes
  2. customthe solvent removed
  3. additionWater was added
  4. extractionthe residue extracted with Et2O
  5. washThe Et2O was washed with brine
  6. customdried
  7. filtrationfiltered
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-437edb3c4cab4f27a8312165adfe4979
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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