Triethyl phosphite → HCID 86605756, compound

HRID 2221707Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[S:6][C:7]=1[CH3:8].[P:22]([O:29]CC)([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25]>>[CH2:24]([O:23][P:22]([CH2:2][C:3]1[N:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[S:6][C:7]=1[CH3:8])([O:26][CH2:27][CH3:28])=[O:29])[CH3:25]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 23076433HCID 23076433, compound

Product 1

HCID 86605756HCID 86605756, compoundYield 58%

Conditions

Temperature: 160 °C

Procedure

A mixture of tert-butyl 4-(4-chloromethyl-5-methyl-1,3-thiazol-2-yl)piperazine-1-carboxylate (2.91 g) and triethyl phosphite (3.20 g) was stirred at 160° C. for 15 hrs. Excess triethyl phosphite was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:2-4:1, v/v) to give tert-butyl 4-{4-[(diethoxyphosphoryl)methyl]-5-methyl-1,3-thiazol-2-yl}piperazine-1-carboxylate as a yellow oil (2.20 g, yield 58%).

Workup

customExcess triethyl phosphite was evaporated under reduced pressure
washeluted with ethyl acetate-hexane (1:2-4:1

Sources & evidence

ORD record: ord-75c3cd287a6343b78fc704b61a64ba28
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368578B2

Reaction notes

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