Ethyl Acetate → HCID 71269627, compound

HRID 1429351Notes

Reaction equation

Cl.[NH2:2][CH:3]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][O:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10].CCN(C(C)C)C(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.CC(=O)OCC>CC#N>[CH2:16]([CH:3]1[NH:2][C:9](=[O:10])[C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[CH2:6][O:5][CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of compound 1c (28 g, 87 mmol) obtained above in CH3CN (1.5 L) was added DIPEA (68 g, 520 mmol) at 0° C., followed by BOP-Cl (70 g, 275 mmol). The resulting mixture was stirred at 0° C. for 30 min and then warmed to rt overnight. The solid was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in EA, washed with 2N HCl and dried over anhydrous Na2SO4. Concentration in vacuo and purification by CC eluting with PE:EA=1:2 gave compound 1d as a yellow oil (7.0 g, 30% yield). 1H NMR (400 MHz, CDCl3): δ 7.50 (dd, J=7.6, 1.6 Hz, 1H), 7.41-7.34 (m, 2H), 7.28-7.19 (m, 4H), 7.05 (d, J=7.2 Hz, 2H), 5.83 (m, 1H), 4.82 (d, J=14.0 Hz, 1H), 4.61 (d, J=13.6 Hz, 1H), 3.82-3.78 (m, 1H), 3.78-3.67 (m, 1H), 3.58-3.55 (m, 1H), 2.75-2.71 (m, 2H). MS (ESI+): 268 [M+1]+.

Workup

temperaturewarmed to rt overnight
customThe solid was removed by filtration
concentrationthe filtrate was concentrated in vacuo
dissolutionThe residue was dissolved in EA
washwashed with 2N HCl
dry with materialdried over anhydrous Na2SO4
concentrationConcentration
customin vacuo and purification by CC
washeluting with PE

Sources & evidence

ORD record: ord-629952a89e5645b68015ba46be032719
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940722B2

Reaction notes

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