tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate → 4-t-Butyloxycarbonylamino-3-hydroxy-6-methyl-1-phenylheptane

HRID 1906362Notes

Reaction equation

HRID 1906362 reaction equation
[C:1]([NH:8][C@H:9]([CH:14]=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:16]([Mg]Br)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[C:4]([O:3][C:1]([NH:8][CH:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[CH:14]([OH:15])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:2])([CH3:6])([CH3:5])[CH3:7]

Participants

4

Reactant 2

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 178419670HCID 178419670, compound

Product 1

HCID 138931534-t-Butyloxycarbonylamino-3-hydroxy-6-methyl-1-phenylheptaneYield 79.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a rapidly stirred -78° C. solution of Boc-Leucinal (1.50 g, 6.97 mmol) in anhydrous ether (10 ml) was added a -78° C. solution of phenethyl magnesium bromide (7 mmol) in anhydrous ether (40 ml) dropwise over the course of 15 minutes, and 45 minutes later the mixture was acidified. The oragnic phase was separated, washed with brine (2×10 ml) and dried (Na2SO4). Filtration and evaporation provided an oil (1.79 g) which was chromatographed with 150 g of 40 m SiO2 (7/3, hexane/ether) to give the desired compound (0.17 g). Mass spectrum: M+ =321.

Workup

  1. customThe oragnic phase was separated
  2. washwashed with brine (2×10 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-f4e083788e07445a8f43d5813ef6bf9c
Source dataset
uspto-grants-1987_03
Patent number
US04652551

Reaction notes

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