Hydrogen Peroxide → [(R)-3-[3-Methoxy-4-(4-phenyl-butoxy)-phenyl]-1-methyl-1-(3-oxo-1,5-dihydro-3lambda*5*-benzo[e][1,3,2]dioxaphosphepin-3-yloxymethyl)-propyl]-carbamic acid tert-butyl ester

HRID 2053462Notes

Reaction equation

HRID 2053462 reaction equation
[C:1]([NH:8][C@:9]([CH2:33]C)([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:16]([O:31][CH3:32])[CH:15]=1)[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)[P:38]1[O:44][CH2:43][C:42]2[CH:45]=[CH:46][CH:47]=[CH:48][C:41]=2[CH2:40][O:39]1)C.N1C=NN=N1.[OH:56]O>C1COCC1>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@:9]([CH3:33])([CH2:10][O:11][P:38]1(=[O:56])[O:39][CH2:40][C:41]2[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=2[CH2:43][O:44]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:16]([O:31][CH3:32])[CH:15]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 41968792,4,3-Benzodioxaphosphepin-3-amine, N,N-diethyl-1,5-dihydro-HCID 12104771n-Boc-(r)-2-amino-2-ethyl-4-[3-methoxy-4-(4-phenyl-butoxy)-phenyl]-butan-1-olHCID 178418441HCID 178418441, compound

Product 1

HCID 59655585[(R)-3-[3-Methoxy-4-(4-phenyl-butoxy)-phenyl]-1-methyl-1-(3-oxo-1,5-dihydro-3lambda*5*-benzo[e][1,3,2]dioxaphosphepin-3-yloxymethyl)-propyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Boc-(R)-2-Amino-2-ethyl-4-[3-methoxy-4-(4-phenyl-butoxy)-phenyl]-butan-1-ol (0.23 g; 0.5 mmol) in THF (5 ml) is added N,N-diethyl-1,5-dihydro-2,4,3-benzodioxaphosphepin-3-amine (0.24 g; 1 mmol) and tetrazole (0.11 g; 1.5 mmol). After 2 hours at RT H2O2 (30% in water; 0.58 ml) is added and the mixture is kept at RT for further two hours. The reaction mixture is quenched with Na2S2O3 and extracted with ethyl acetate and then washed with aqueous citric acid and aqueous saturated NaHCO3 solution. The organic layer is dried and concentrated and then purified on a silica gel using dichloromethane/ethanol (95/5) as mobile phase.

Workup

  1. customThe reaction mixture is quenched with Na2S2O3
  2. extractionextracted with ethyl acetate
  3. washwashed with aqueous citric acid and aqueous saturated NaHCO3 solution
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. custompurified on a silica gel

Sources & evidence

ORD record
ord-3cfdffc33a39494aafa46533749d0f92
Source dataset
uspto-grants-2008_02
Patent number
US07326801B2

Reaction notes

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