(L)-ethyl lactate → 2-({4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phenoxy-phosphinoyloxy)-propionic Acid Ethyl Ester

HRID 33019

Reaktionsgleichung

Reaktionsgleichung von HRID 33019
[C:1]1([O:7][P:8]([CH2:11][C:12]([CH3:35])=[CH:13][CH2:14][C:15]2[C:16]([O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])=[C:17]3[C:21](=[C:22]([CH3:26])[C:23]=2[O:24][CH3:25])[CH2:20][O:19][C:18]3=[O:27])(=[O:10])[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:36]([O:41][CH2:42][CH3:43])(=[O:40])[C@H:37]([CH3:39])O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1>[CH2:42]([O:41][C:36](=[O:40])[CH:37]([O:10][P:8]([CH2:11][C:12]([CH3:35])=[CH:13][CH2:14][C:15]1[C:16]([O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:32])[CH3:33])=[C:17]2[C:21](=[C:22]([CH3:26])[C:23]=1[O:24][CH3:25])[CH2:20][O:19][C:18]2=[O:27])([O:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:9])[CH3:39])[CH3:43]

Komponenten

5

Edukt 3

HCID 92831(L)-ethyl lactateHCID 2724699PyBOPHCID 76548829{4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Monophenyl Ester

Produkt 1

HCID 765462022-({4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phenoxy-phosphinoyloxy)-propionic Acid Ethyl EsterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of {4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic acid monophenyl ester (25 mg, 0.048 mmol) and ethyl (S)-(−)-lactate (34 mg, 0.288 mmol) in pyridine (1 mL) was added PyBOP (125 mg, 0.24 mmol). The solution was stirred at room temperature for 16 hours and concentrated. The residue was purified by RP HPLC using a C18 column with a gradient of H2O, 0.1% TFA-acetonitrile, 0.1% TFA to provide 24 mg (83%) of the desired product. MS (m/z) 641 [M+Na]+.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was purified by RP HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8a947f7021f84321aabea44ce377ef1f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427636B2

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