Diisopropyl Ether → 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(p-methoxy-phenylmethyl)-dihydrofuran-2-(3H)-one

HRID 1376659Notes

Reaction equation

HRID 1376659 reaction equation
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[CH2:19][CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]I)=[CH:37][CH:36]=1.C(OC(C)C)(C)C>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:39][C:38]2[CH:41]=[CH:42][C:35]([O:34][CH3:33])=[CH:36][CH:37]=2)[CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 2733832Lithium HexamethyldisilazideHCID 10870461tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamateHCID 11746977p-Methoxybenzyl iodide

Product 1

HCID 677185285(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(p-methoxy-phenylmethyl)-dihydrofuran-2-(3H)-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

2.98 g (9.74 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-dihydrofuran-2-(3H)-one dissolved in 40 ml of THF are deprotonated at -75° C. with 19.5 ml of lithium bis(trimethylsilyl)amide 1M in THF and alkylated with 2.9 g (11.7 mmol) of p-methoxybenzyl iodide in 20 ml of THF (45 min). Column chromatography (SiO2, hexane/ethyl acetate 2:1) and digestion using diisopropyl ether yield the pure title compound; TLC Rf (D)=0.32; tRet (I)=16.7 min.

Sources & evidence

ORD record
ord-5f42dba7011f46a69403b94c869bbb64
Source dataset
uspto-grants-1997_09
Patent number
US05663168

Reaction notes

Loading…