Benzoyl chloride → HCID 58840909, compound

HRID 1268830Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH2:26])[C:13](=[O:25])[NH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)([CH3:4])([CH3:3])[CH3:2].[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>CC#N>[C:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:26][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:13](=[O:25])[NH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of (7S)-7-amino-7-(quinolin-6-ylcarbamoyl)-heptanoic acid tert-butyl ester (8.0 g, 21.6 mmol) in dry MeCN (100 mL) and to this solution was added benzoyl chloride (2.78 mL, 23.8 mmol) and triethylamine (6.1 mL, 43.2 mmol). The solution was stirred at 0° C. for 1 h, then at RT for 2 h. The solvent was removed, and residue was dissolved in 400 mL EtOAc, and stirred with 100 mL 0.5 M NaHCO3 for 1 h. The aqueous layer was removed, and the organic layer was washed with 100 mL 0.5 M NaHCO3, then with 50 mL water. The solution was dried over anhydrous Na2SO4. The product (8.1 g) was obtained after column purification (EtOAc as eluent) in 78.8% yield as a thick oil. 1H NMR (CDCl3) δ 9.40 (1H, s), 8.80 (1H, d), 8.22 (1H, d), 8.0–7.0 (10H, m), 5.0 (1H, m), 2.2–1.2 (19H, m). MS (ESI): (MH+) 476.1.

Workup

waitat RT for 2 h
customThe solvent was removed
dissolutionresidue was dissolved in 400 mL EtOAc
stirringstirred with 100 mL 0.5 M NaHCO3 for 1 h
customThe aqueous layer was removed
washthe organic layer was washed with 100 mL 0.5 M NaHCO3
dry with materialThe solution was dried over anhydrous Na2SO4

Sources & evidence

ORD record: ord-4221ec2f11624dd7a24700d332b2c5d6
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199134B2

Reaction notes

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