Methyl chloroformate → HCID 11951669, compound

HRID 2114905Notes

Reaction equation

Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][CH2:7][C@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:15]=[C:16]3[C:20](=[C:21]([F:23])[CH:22]=2)[N:19](CC2CC2)[C:18](=[O:28])[CH2:17]3)[CH2:9]1.C(N([CH:35]([CH3:37])[CH3:36])CC)(C)C>ClCCl>[CH3:5][O:4][C:2](=[O:3])[NH:6][CH2:7][C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:15]=[C:16]3[C:20](=[C:21]([F:23])[CH:22]=2)[N:19]([CH:35]2[CH2:37][CH2:36]2)[C:18](=[O:28])[CH2:17]3)[CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl chloroformate (0.070 ml, 0.858 mmol) is added dropwise to (R)-5-(5-aminomethyl-2-oxo-oxazolidin-3-yl)-1-cyclopropylmethyl-7-fluoro-1,3-dihydro-indol-2-one (0.300 g, 0.709 mmol) and diisopropylethylamine (0.37 ml, 2.13 mmol) in dichloromethane (15 ml) at 0° C. The reaction is stirred at 0° C. for 30 minutes and then allowed to warm at room temperature. The reaction mixture is diluted with dichloromethane, washed with water and brine, dried (Na2SO4) and evaporated. The residue is purified by PTLC (10% MeOH/DCM) to give the title compound as an off white solid. HPLC r.t. 4.55 min; 1H NMR (300 MHz, CDCl3) 7.52 (1H), 7.39 (s, H), 7.35 (s, 1H), 4.68-4.66 (m, 1H), 4.09 (t, J=9.0 Hz, 1H), 3.74 (dd, J=9, 6 Hz, 1H), 3.69 (s, 2H), 3.59 (d, J=7.2 Hz, 2H), 3.53 (s, 3H), 3.33 (t, J=5.4 Hz, 2H), 1.26-1.23 (m, 1H), 0.47-0.42 (m, 2H), 0.32-0.29 (m, 2H); MS for C18H20FN3O5 m/z 378.1(M+H)+.

Workup

temperatureto warm at room temperature
washwashed with water and brine
dry with materialdried (Na2SO4)
customevaporated
customThe residue is purified by PTLC (10% MeOH/DCM)

Sources & evidence

ORD record: ord-540a3f5c081d44d1a64ac8298ff3f9d6
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435751B2

Reaction notes

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