Chloroacetonitrile → HCID 72700451, compound

HRID 2208642Notes

Reaction equation

Cl[CH2:2][C:3]#[N:4].CCN(C(C)C)C(C)C.[N:14]([CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([O-:20])=[O:19])=[N+:15]=[N-:16]>>[N:14]([C@@H:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([O:20][CH2:2][C:3]#[N:4])=[O:19])=[N+:15]=[N-:16]

Participants

Reactant 3

HCID 7856Chloroacetonitrile

HCID 81531Diisopropylethylamine

HCID 90018785HCID 90018785, compound

Product 1

HCID 72700451HCID 72700451, compoundYield 50%

Procedure

Chloroacetonitrile (1 mL) and DIPEA (310 mg, 0.411 mL, 2.41 mmol) were added to 2-azido-3-phenylpropanoate and stirred for 12 h. The solvent was removed under reduced pressure and SiO2 flash chromatography (40-50% ethyl acetate in hexanes) afforded (250 mg) of a white solid in 50% yield. Rf 0.5 in 50% ethyl acetate in hexanes; 1H NMR (500 MHz, CDCl3) δ 7.37 (t, J=7.6 Hz, 2H), 7.32-7.29 (m, 1H), 7.25 (t, J=7.6 Hz, 2H), 4.77 (t, J=1.0 Hz, 1H), 4.18 (dd, J=6.2, 1.8 Hz, 1H), 3.21 (dd, J=14.0, 5.8 Hz, 1H), 3.08 (dd, J=13.9, 8.4 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 168.8, 135.1, 129.3, 129.1, 127.8, 113.7, 62.9, 49.3, 37.7; HRMS (ESI) m/z calcd for C11H10N4O2Na [M+Na]+ 253.070. found 253.071.

Workup

customThe solvent was removed under reduced pressure and SiO2 flash chromatography (40-50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-7672e895c0204069b0e61b16dcfd4793
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376700B2

Reaction notes

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