Potassium Iodide → Ethyl 2-(tert-butoxycarbonylamino)-2-cyano-3-[(-)-menthyloxycarbonyl]propionate

HRID 1661871Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:26][C:27]([O:29][CH:30]1[CH:35]([CH:36]([CH3:38])[CH3:37])[CH2:34][CH2:33][CH:32]([CH3:39])[CH2:31]1)=[O:28]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][C:9]([C:15]#[N:16])([CH2:26][C:27]([O:29][CH:30]1[CH:35]([CH:36]([CH3:38])[CH3:37])[CH2:34][CH2:33][CH:32]([CH3:39])[CH2:31]1)=[O:28])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 15 °C

Procedure

Ethyl 2-(tert-butoxycarbonylamino)-2-cyanoacetate (1.20 g, 526 mmol) prepared in the same manner as Reference Example 1, acetone (2.3 ml), powdered potassium carbonate (872 mg, 6.31 mmol) and potassium iodide (175 mg, 1.05 mmol) were mixed, a solution of menthyl chloroacetate (1.22 g, 5.26 mmol) dissolved in acetone (1.1 ml) was added dropwise thereto at 10-20° C., and the mixture was stirred at the same temperature overnight. Insoluble materials were removed by filtration, the filtrate was concentrated in vacuo and toluene was added to the residue. The organic layer was washed with water and concentrated in vacuo to give ethyl 2-(tert-butoxycarbonylamino)-2-cyano-3-[(−)menthyloxycarbonyl]propionate (1.10 g, yield 49.3%) as a yellow oil.

Workup

additionwere mixed
additionwas added dropwise
customInsoluble materials were removed by filtration
concentrationthe filtrate was concentrated in vacuo and toluene
additionwas added to the residue
washThe organic layer was washed with water
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c88a3cb1041449febed0dea1a014a3c0
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030486B2

Reaction notes

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