Chloroacetonitrile → HCID 72700533, compound

HRID 2208643Notes

Reaction equation

Cl[CH2:2][C:3]#[N:4].CCN(C(C)C)C(C)C.[C:14]([NH:21][C@H:22]([C:38]([OH:40])=[O:39])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][C@H:22]([NH:21][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:38]([O:40][CH2:2][C:3]#[N:4])=[O:39])=[CH:25][CH:26]=1)(=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

Reactant 3

HCID 7856Chloroacetonitrile

HCID 81531Diisopropylethylamine

HCID 7015809Boc-4-benzoyl-L-phenylalanine

Product 1

HCID 72700533HCID 72700533, compoundYield 93%

Procedure

Chloroacetonitrile (1 mL) and DIPEA (20 mg, 34 μL, 0.21 mmol) were added to Boc-p-benzoylphenylalanine (61 mg, 0.19 mmol). The reaction was stirred for 18 h, then concentrated under reduced pressure. SiO2 flash chromatography (40% ethyl acetate in hexanes) afforded 70 mg of a pale yellow oil in 93% yield. Rf 0.5 in 50% ethyl acetate in hexanes. 1H NMR (500 MHz, CDCl3) δ 7.79 (dd, J=7.1, 4.9 Hz, 4H), 7.59 (t, J=7.6 Hz, 1H), 7.48 (t, J=7.6 Hz, 2H), 7.29 (d, J=8.0 Hz, 2H), 5.00 (d, J=7.4 Hz, 1H), 4.83 (d, J=15.7 Hz, 1H), 4.72-4.69 (m, 2H), 3.25 (dd, J=13.7, 5.8 Hz, 1H), 3.16 (dd, J=13.1, 6.5 Hz, 1H), 1.43 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 196.4, 170.6, 155.1, 140.3, 137.6, 136.9, 132.7, 130.8, 130.2, 129.4, 128.5, 113.9; HRMS (ESI) m/z calcd for C23H24N2NaO5 [M+Na]+ 431.158. found 431.158.

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-38f0249064a541f4976ee1cdcf25314b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376700B2

Reaction notes

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