Dimethyl methylphosphonate → (7-tert-Butoxycarbonylamino-2-oxo-heptyl)-phosphonic acid dimethyl ester

HRID 860092Notes

Reaction equation

[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.O=C1CCC(=O)N1[O:20][C:21](=O)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>C1COCC1>[CH3:4][O:3][P:2]([CH2:1][C:21](=[O:20])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])(=[O:7])[O:5][CH3:6]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of dimethyl methylphosphonate (9.308 g, 75.01 mmol) in THF (30 mL) was cooled to −78 ° C. and treated with n-butyllithium (29.5 mL of 2.5 M). The reaction mixture was stirred at −78 ° C. for 10 min, followed by addition of 6-tert-butoxycarbonylamino-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (24-1) (5.060 g, 15.41 mmol) in THF (30 mL). After 15 min the reaction was quenched with aqueous NH4Cl and allowed to warm to room temperature overnight. The water was extracted three times with ethyl acetate and the combined organics washed with brine and dried (Na2SO4). The solvent was removed in vacuo to afford the title compound 24-2 as a pale yellow oil (5.5 g).

Workup

customAfter 15 min the reaction was quenched with aqueous NH4Cl
temperatureto warm to room temperature overnight
extractionThe water was extracted three times with ethyl acetate
washthe combined organics washed with brine
dry with materialdried (Na2SO4)
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-632d255c771449be809672fa3420dff6
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153862B2

Reaction notes

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