Chlorosuccinimide → HCID 25135999, compound

HRID 2250293Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11](=[O:35])[C@H:12]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:13][C:14]1[CH:23]=[CH:22][C:17]2[NH:18][C:19](=[O:21])[O:20][C:16]=2[CH:15]=1>C(O)(=O)C>[CH3:9][O:10][C:11](=[O:35])[C@H:12]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[CH2:13][C:14]1[C:23]([Cl:1])=[CH:22][C:17]2[NH:18][C:19](=[O:21])[O:20][C:16]=2[CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N-Chlorosuccinimide (315 mg, 2.36 mmol) was added to a solution of (R)-2-benzyloxycarbonylamino-3-(2-oxo-2,3-dihydro-benzooxazol-6-yl)-propionic acid methyl ester (700 mg, 1.89 mmol) in acetic acid (50 mL) at room temperature. The mixture was heated at 100° C. for 16 h. After it was cooled down to room temperature, solvents were removed in vacuo. The residue was subjected to silica gel chromatography using ethyl acetate/hexanes (4:6) then (1:1) as eluent to afford the title compound as an off-yellow solid (242 mg, 32%). The structure of the product was confirmed by 2D NMR. 1H-NMR (CD3COCD3, 500 MHz) δ 10.47 (s, 1H), 7.36-7.28 (m, 6H), 7.20 (s, 1H), 6.80 (d, J=8.5 Hz, 1H), 5.05 (d, J=12.5 Hz, 1H), 5.00 (d, J=12.5 Hz, 1H), 4.65-4.60 (m, 1H), 3.73 (s, 3H), 3.43 (dd, J=14.0, 5.0 Hz, 1H), 3.08 (dd, J=14.0, 10.5 Hz, 1H); 13C-NMR (CD3COCD3, 125 MHz) δ 172.2, 156.5, 154.5, 143.1, 137.5, 130.8, 129.0, 128.9, 128.7, 128.2, 128.0, 112.8, 110.9, 66.3, 54.3, 52.1, 35.8; Mass spec. 405 (MH+).

Workup

temperatureAfter it was cooled down to room temperature
customsolvents were removed in vacuo

Sources & evidence

ORD record: ord-21d8f91c970940adba9e961bb5c6473c
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314883B2

Reaction notes

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