Water → 3(R)-[(4-Benzyloxyphenyl)methyl]-5(S)-[1(S)-(Boc-amino)-2-cyclohexylethyl]dihydrofuran-2-one

HRID 1585370Notes

Reaction equation

HRID 1585370 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][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:23]([O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]I)=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(=O)CC.O>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH2:23]([O:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:35][C@@H:19]2[CH2:18][C@@H:17]([C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])[CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[O:21][C:20]2=[O:22])=[CH:37][CH:38]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1032Propionic AcidHCID 10946873(5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-oneHCID 11723738p-Benzyloxybenzyl iodide

Product 1

HCID 566153103(R)-[(4-Benzyloxyphenyl)methyl]-5(S)-[1(S)-(Boc-amino)-2-cyclohexylethyl]dihydrofuran-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

In analogy with Example 1h), 5.2 g (16.7 mmol) of 5(S)-[1(S)-(Boc-amino)-2-cyclohexylethyl]dihydrofuran-2-one (Example 12a)), dissolved in 50 ml of THF, are deprotonated, at -70° C., with 33.4 ml of a 1M solution of lithium is(trimethylsilyl)amide in THF, and alkylated (at -75° C. for 1 h) with 5.2 g (16.07 mmol) of p-benzyloxybenzyl iodide [preparation, see Example 1d)] in 15 ml of THF. Adding 6.2 ml (83.02 mmol) of propionic acid and water at -75° C., and further working up, affords the title compound after column chromatography (SiO2, hexane/ethyl acetate: 4:1). TLC Rf (hexane/ethyl acetate: 4:1)=0.27; tRet (II)=20.41 min.

Workup

  1. custom(at -75° C. for 1 h)
  2. custompreparation

Sources & evidence

ORD record
ord-afe82377e39947c193e77b8f2992c0d2
Source dataset
uspto-grants-1999_08
Patent number
US05935976

Reaction notes

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