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

HRID 426024Notes

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, 5.26 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-1efb744e37ec4aba8c611620a1cce11c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106230B2

Reaction notes

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