(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

Reaction equation

HRID 33019 reaction equation
[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]

Participants

5

Reactant 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

Product 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 EsterYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-8a947f7021f84321aabea44ce377ef1f
Source dataset
uspto-grants-2008_09
Patent number
US07427636B2

Linked notes

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