Chloroacetonitrile → HCID 72700450, compound

HRID 2208641Notes

Reaction equation

HRID 2208641 reaction equation
Cl[CH2:2][C:3]#[N:4].CCN(C(C)C)C(C)C.[C:14]([N:21]([CH3:33])[C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>O1CCCC1>[C:17]([O:16][C:14]([N:21]([CH3:33])[C@@H:22]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:30]([O:32][CH2:2][C:3]#[N:4])=[O:31])=[O:15])([CH3:18])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 81531DiisopropylethylamineHCID 7010602Boc-N-Me-Phe-OH

Product 1

HCID 72700450HCID 72700450, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chloroacetonitrile (1.1 mL) and DIPEA (258 mg, 0.341 mL, 1.99 mmol) were added to Boc-MePhe-OH (497 mg, 1.78 mmol) in tetrahydrofuran (5 mL) and stirred for 12 h. The solvent was removed under reduced pressure and SiO2 flash chromatography (20-35% ethyl acetate in hexanes) afforded 505 mg of a pale yellow oil in 89% yield. Rf 0.3 in 20% ethyl acetate in hexanes; 1H NMR (500 MHz, CDCl3): δ 7.28-7.25 (m, 2H), 7.20-7.16 (m, 3H), 4.72-4.68 (m, 2H), 4.53-4.52 (m, 1H), 3.27 (m, 1H), 3.11-3.02 (m, 1H), 2.67 (d, J=17 Hz, 3H), 1.36 (d, J=12 Hz, 9H); 13C NMR (125 MHz, CDCl3): δ 169.9, 155.5, 136.8, 128.9, 128.6, 128.4, 126.8, 126.7, 114.2, 80.8, 61.5, 48.7, 35.4, 33.0, 28.1; HRMS (ESI) m/z calcd for C17H22N2O4Na [M+Na]+ 341.147. found 341.149.

Workup

  1. customThe solvent was removed under reduced pressure and SiO2 flash chromatography (20-35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-78010e7950df48198202e8a1e5f3647c
Source dataset
uspto-grants-2016_06
Patent number
US09376700B2

Reaction notes

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