Propionic Acid → HCID 67709378, compound

HRID 2394098Notes

Reaction equation

HRID 2394098 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+].[Cl:33][C:34]1[CH:51]=[CH:50][CH:49]=[C:48]([Cl:52])[C:35]=1[CH2:36][S:37]([C:40]1[CH:47]=[CH:46][C:43]([CH2:44]Br)=[CH:42][CH:41]=1)(=[O:39])=[O:38].C(O)(=O)CC>C1COCC1.O.CCCCCC.C(OCC)(=O)C.CN1C(=O)N(C)CCC1>[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:44][C:43]2[CH:42]=[CH:41][C:40]([S:37]([CH2:36][C:35]3[C:34]([Cl:33])=[CH:51][CH:50]=[CH:49][C:48]=3[Cl:52])(=[O:39])=[O:38])=[CH:47][CH:46]=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

9

Reactant 4

HCID 1032Propionic AcidHCID 2733832Lithium HexamethyldisilazideHCID 10870461tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamateHCID 222694282-{[4-(Bromomethyl)benzene-1-sulfonyl]methyl}-1,3-dichlorobenzene

Product 1

HCID 67709378HCID 67709378, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-SolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

In analogy with Example 5d), 5.0 g (16.34 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]dihydrofuran-2-(3H)-one, dissolved in 24 ml of abs. THF and 2.7 ml of DMPU, are deprotonated, at -75° C., with 32.7 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF, and alkylated, at -75° C., with 9.67 g (24.5 mmol) of p-(2,6-dichlorobenzylsulfonyl)benzyl bromide (Maybridge; Tintagel/UK) in 50 ml of abs. THF. Protonation, at -75° C., with 6.1 ml (81.7 mmol) of propionic acid and 6.1 ml of water, extraction and column chromatography (SiO2, hexane/ethyl acetate, 2:1) of the crude product, and crystallization from DIPE, affords the title compound: TLC Rf (D)=0.30; tRet (II)=17.3 min.

Sources & evidence

ORD record
ord-7fd953f734cf48ffb5d45a69073f187d
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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