Methyl chloroformate → HCID 11842691, compound

HRID 2114876Notes

Reaction equation

HRID 2114876 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][CH2:7][CH: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:24]([CH3:26])[CH3:25])[C:18](=[O:27])[CH2:17]3)[CH2:9]1.C(N(C(C)C)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:24]([CH3:25])[CH3:26])[C:18](=[O:27])[CH2:17]3)[CH2:9]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 69274161HCID 69274161, compound

Product 1

HCID 11842691HCID 11842691, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl chloroformate (0.097 ml, 1.26 mmol) is added dropwise to 5-(5-aminomethyl-2-oxo-oxazolidin-3-yl)-7-fluoro-1-isopropyl-1,3-dihydro-indol-2-one (21, 0.355 g, 0.842 mmol) and diisopropylethylamine (0.616 ml, 3.37 mmol) in dichloromethane (4 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, citric acid and brine, dried (Na2SO4) and evaporated. The residue is purified to give the title compound as a solid. HPLC r.t. 4.42 min; 1H NMR (300 MHz, CDCl3) δ7.33 (d, J=1.2 Hz, 1H), 7.24 (dd, J=2.1, 14 Hz, 1H), 5.14 (br s, 1H), 4.80-4.92 (m, 1H), 4.75-4.84 (m, 1H), 4.05 (t, J=8.7 Hz, 1H), 3.81 (dd, J=6.6, 9 Hz, 1H), 3.71 (s, 3H), 3.57 (s, 2H), 3.52-3.65 (m, 2H), 1.44 (d, J=6.9 Hz, 6H); MS for C17H20FN3O5 m/z 366 (M+H)+.

Workup

  1. temperatureto warm at room temperature
  2. washwashed with water, citric acid and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue is purified

Sources & evidence

ORD record
ord-914ff45b3ec54662b8d18cc5a0f4e3be
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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