HCID 10893253, compound → Cbz-L-Phenylalaninal

HRID 504158Notes

Reaction equation

HRID 504158 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15](=[O:31])[NH:16][C@H:17]([C:25](=[O:30])N(OC)C)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([O:14][C:15](=[O:31])[NH:16][C@@H:17]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:25]=[O:30])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 10893253HCID 10893253, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 7021150Cbz-L-PhenylalaninalYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (0.95 mL of a 1.0 M solution in THF, 0.95 mmoles) was added to a room temperature solution of [(S)-1-(Methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (0.30 g, 0.86 mmoles) in THF (10 mL). The resulting mixture was stirred at room temperature for 2 h, then was quenched by dilution with EtOAc (200 mL), and washed with 1% aqueous HCl (200 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was repeatedly diluted with CH3CN (2×200 mL) and concentrated in vacuo to give 0.24 g (approximately quantitative yield) of ((S)-1-Benzyl-2-oxo-ethyl)-carbamic acid benzyl ester as a colorless oil, which was carried on without further purification: ES+ LC/MS m/e 284 (M+H), RT=4.75 min.

Workup

  1. customwas quenched by dilution with EtOAc (200 mL)
  2. washwashed with 1% aqueous HCl (200 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. additionThe residue was repeatedly diluted with CH3CN (2×200 mL)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b514a1bb59fe4dfd9bdaa37005385101
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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