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 2053462노트

반응식

HRID 2053462 반응식
[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]

참가 물질

6

반응물 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, 화합물

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3cfdffc33a39494aafa46533749d0f92
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326801B2

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