Chloroacetonitrile → HCID 72700447, compound

HRID 2208640Notes

Reaction equation

Cl[CH2:2][C:3]#[N:4].CCN(C(C)C)C(C)C.[NH:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18]>>[C:26]([O:25][C:23]([NH:14][C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:20]([O:22][CH2:2][C:3]#[N:4])=[O:21])=[O:24])([CH3:27])([CH3:29])[CH3:28]

Participants

Reactant 3

HCID 7856Chloroacetonitrile

HCID 81531Diisopropylethylamine

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 72700447HCID 72700447, compoundYield 96%

Procedure

Chloroacetonitrile (5 mL) and DIPEA (160 mg, 0.21 mL, 1.2 mmol) were added to Boc-Leu-OH (252 mg, 1.09 mmol) and stirred for 12 h. The solvent was removed under reduced pressure and SiO2 flash chromatography (20% ethyl acetate in hexanes) afforded 284 mg of a pale yellow oil in 96% yield. Rf 0.5 in 20% ethyl acetate in hexanes. 1H NMR (500 MHz, CDCl3): δ 5.00 (d, J=7.7 Hz, 1H), 4.80-4.65 (m, 2H), 4.30-4.29 (m, 1H), 1.70-1.65 (m, 1H), 1.60-1.47 (m, 2H), 1.39 (s, 9H), 0.91-0.89 (m, 6H); 13C NMR (125 MHz, CDCl3): δ 172.2, 155.5, 114.21, 80.3, 53.2, 52.0, 41.0, 28.3, 24.8, 22.8, 21.7; HRMS (ESI) m/z calcd for C13H22N2O4Na [M+Na]+ 293.147. found 293.151.

Workup

customThe solvent was removed under reduced pressure and SiO2 flash chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-2479238ccfc5485e9fec94bff6e52aac
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376700B2

Reaction notes

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