Methyl chloroformate → HCID 11951669, compound

HRID 2114901Notes

Reaction equation

HRID 2114901 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]([CH:24]2[CH2:26][CH2:25]2)[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]2[CH2:26][CH2:25]2)[C:18](=[O:27])[CH2:17]3)[CH2:9]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 69272770HCID 69272770, compound

Product 1

HCID 11951669HCID 11951669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl chloroformate (0.055 ml, 0.715 mmol) is added dropwise to (R)-5-(5-aminomethyl-2-oxo-oxazolidin-3-yl)-1-cyclopropyl-7-fluoro-1,3-dihydro-indol-2-one (Example 50, Step 5, 0.200 g, 0.476 mmol) and diisopropylethylamine (0.349 ml, 1.90 mmol) in dichloromethane (5 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 (5% MeOH/DCM) to give the title compound as a yellow solid. HPLC r.t. 4.05 min; 1H NMR (300 MHz, CDCl3) 7.23 (m, 1H), 7.18 (m, 1H), 5.12 (t, 1H), 4.77 (m, 1H), 4.02 (t, J=8.7 Hz, 1H), 3.79 (dd, J=6.6, 9 Hz, 1H), 3.69 (s, 3H), 3.51 (m, 2H), 2.85 (m, 1H), 0.97 (m, 2H); MS for C17H18FN3O5 m/z 364.0 (M+H)+.

Workup

  1. temperatureto warm at room temperature
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue is purified by PTLC (5% MeOH/DCM)

Sources & evidence

ORD record
ord-c078cefce06744f3928ed74d5c141be7
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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