Chlorosuccinimide → HCID 66695391, compound

HRID 2367992Notes

Reaction equation

[OH:1][B:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:24][N+:25]([O-:27])=[O:26])[O:3]1.C1C(=O)N([Cl:35])C(=O)C1>CN(C=O)C>[C:19]([O:18][C:17](=[O:23])[NH:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:7]1[C:6]2[B:2]([OH:1])[O:3][CH:4]([CH2:24][N+:25]([O-:27])=[O:26])[C:5]=2[C:10]([Cl:35])=[CH:9][CH:8]=1)([CH3:21])([CH3:22])[CH3:20]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl 4-(1-hydroxy-3-(nitromethyl)-1,3-dihydrobenzo[c][1,2]oxaborol-7-yloxy)-butylcarbamate (640 mg, 1.7 mmol) in DMF (20 mL) was added NCS (226 mg, 1.7 mmol) in DMF (5 mL). The mixture was heated to 80° C. for 2 h. After the reaction was quenched with an aqueous LiCl solution (100 mL), the resulting mixture was extracted with EtOAc (3×50 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep-HPLC to give the product (280 mg, yield 67.5%). 1H NMR (400 MHz, DMSO-d6) δ 9.29 (s, 1H), 7.47-7.49 (d, 1H), 6.96-6.98 (d, 1H), 6.80 (s, 1H), 5.74-5.77 (m, 1H), 5.31-5.35 (m, 1H), 4.67-4.72 (m, 1H), 4.02-4.05 (m, 2H), 2.94-2.99 (m, 2H), 1.68-1.72 (m, 2H), 1.50-1.56 (m, 2H), 1.36 (s, 9H).

Workup

customAfter the reaction was quenched with an aqueous LiCl solution (100 mL)
extractionthe resulting mixture was extracted with EtOAc (3×50 mL)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by prep-HPLC

Sources & evidence

ORD record: ord-b0db9145360f452aaa3726c82b4f9326
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703742B2

Reaction notes

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