Benzoyl chloride → HCID 86701261, compound

HRID 2276062Notes

Reaction equation

HRID 2276062 reaction equation
[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH2:17][OH:18])[C:14](=[O:19])[O:13][CH2:12][C@H:11]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10](=[O:28])[O:9][C@H:8]1[CH3:29])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>N1C=CC=CC=1.C(Cl)Cl>[C:30]([O:18][CH2:17][CH2:16][C@@H:15]1[C@@H:7]([O:6][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[C@H:8]([CH3:29])[O:9][C:10](=[O:28])[C@@H:11]([NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:12][O:13][C:14]1=[O:19])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 86701260HCID 86701260, compound

Product 1

HCID 86701261HCID 86701261, compoundYield 107.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,6S,7R,8R)-3-(tert-butoxycarbonylamino)-8-(2-hydroxyethyl)-6 methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (200 mg, 0.479 mmol) in pyridine (0.5 mL) and CH2Cl2 (1 mL) was added benzoyl chloride (195 mg, 0.958 mmol) at room temperature (about 22° C.), and the reaction mixture was stirred at room temperature for 12 h. The solvents were removed under vacuum and the residue was purified by column chromatography (SiO2, hexanes/EtOAc gradient) to give the title compound (268 mg, 74%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.97 (dd, J=8.5, 1.0 Hz, 2H), 7.56-7.40 (m, J=10.6, 3H), 5.39-5.15 (m, 2H), 5.10 (t, J=9.9 Hz, 1H), 4.97-4.73 (m, 2H), 4.42-4.29 (m, 1H), 4.25 (m, 1H), 3.57-3.35 (m, 1H), 2.73 (t, J=9.5 Hz, 1H), 2.62 (dt, J=14.0, 7.0 Hz, 1H), 2.36-2.18 (m, 1H), 1.90-1.71 (m, 1H), 1.46 (s, 9H), 1.28 (d, J=6.4 Hz, 3H), 1.21 (dd, J=7.0, 1.0 Hz, 6H); ESIMS m/z 544 ([M+Na]+).

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was purified by column chromatography (SiO2, hexanes/EtOAc gradient)

Sources & evidence

ORD record
ord-7e7ce995ba964296999e75edc9468679
Source dataset
uspto-grants-2015_09
Patent number
US09131690B2

Reaction notes

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