Benzyl Bromide → 5(S)-[1(S)-(Boc-Amino)-2-(p-methoxyphenyl)ethyl]-3(R)-(phenylmethyl)dihydrofuran-2-(3H)-one
Reaction equation
C(N[C@H]([C@H]1OC(=O)CC1)CC1C=CC(OC)=CC=1)(OC(C)(C)C)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:35]([NH:42][C@H:43]([C@H:59]1[O:63][C:62](=[O:64])[C@H:61]([CH2:65][C:66]2[CH:71]=[CH:70][C:69](OCC3C=CC=CC=3)=[CH:68][CH:67]=2)[CH2:60]1)[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH2:52]C2C=CC=CC=2)=[CH:47][CH:46]=1)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].C(Br)C1C=CC=CC=1>C1COCC1.CN1C(=O)N(C)CCC1>[C:35]([NH:42][C@H:43]([C@H:59]1[O:63][C:62](=[O:64])[C@H:61]([CH2:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH2:60]1)[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
In analogy with Example 5d), 4.17 g (12.44 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-methoxyphenyl)ethyl]dihydrofuran-2-(3H)-one, dissolved in 22.4 ml of THF and 2.5 ml of DMPU, are deprotonated, at -70° C., with 24 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF, and alkylated -75° C., 1h) with 1.5 ml (12.44 mmol) of benzyl bromide. Protonation, at -75° C., with 4.6 ml of propionic acid and 4.6 ml of water, extraction and column chromatography (SiO2, methylene chloride/ether 25:1) yields the title compound: TLC Rf (C)=0.74; tRet (II)=16.6 min; FAB-MS (M+H)+ =426.
Workup
- extractionProtonation, at -75° C., with 4.6 ml of propionic acid and 4.6 ml of water, extraction and column chromatography (SiO2, methylene chloride/ether 25:1)
Sources & evidence
- ORD record
- ord-d3548c706bb649ada0242c1d791a9eb8
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05807891
Reaction notes
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