{(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester → {(1R,2R)-2-benzyloxy-1-[2-(4-chlorophenyl)-2-oxoethoxymethyl]propyl}carbamic acid t-butyl ester

HRID 16375

Reaction equation

HRID 16375 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([CH2:19][O:20][CH2:21][C:22](=[O:27])NCOC)[C@H:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([Mg]Br)=[CH:32][CH:31]=1>O1CCCC1.[Cl-].[NH4+]>[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([CH2:19][O:20][CH2:21][C:22]([C:33]1[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=1)=[O:27])[C@H:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 67379173{(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl esterHCID 178478191HCID 178478191, compound

Product 1

HCID 67373088{(1R,2R)-2-benzyloxy-1-[2-(4-chlorophenyl)-2-oxoethoxymethyl]propyl}carbamic acid t-butyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of {(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester (2.42 g) in tetrahydrofuran (50 mL) was cooled to −40° C. and to the mixture was then dropwise added 4-chlorophenylmagnesium bromide (18.3 mL, 1 M tetrahydrofuran solution). The resultant solution was stirred for 1 hour at −40° C., after which the temperature was slowly raised to 0° C. The solution was then diluted with saturated aqueous ammonium chloride. The resultant solution was extracted using ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/1), to thereby obtain the titled compound (2.61 g). The physical properties of this crude product were as follows.

Workup

  1. extractionThe resultant solution was extracted
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customSolvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/1)

Sources & evidence

ORD record
ord-4c957e16d1a84e578fc1b0ae8c2d812d
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Linked notes

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