Methyl chloroformate → HCID 22961826, compound

HRID 365929Notes

Reaction equation

HRID 365929 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([O:10][CH2:11][C@@H:12]2[CH2:15][CH2:14][N:13]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[N:7][C:8]=1[Cl:9].CCN(CC)CC.Cl[C:31]([O:33][CH3:34])=[O:32]>C(Cl)Cl>[C:16]([N:13]1[CH2:14][CH2:15][C@H:12]1[CH2:11][O:10][C:5]1[CH:6]=[N:7][C:8]([Cl:9])=[C:3]([CH2:2][NH:1][C:31]([O:33][CH3:34])=[O:32])[CH:4]=1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 22872662HCID 22872662, compound

Product 1

HCID 22961826HCID 22961826, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Aminomethyl-3-(1-BOC-2-(S)-azetidinylmethoxy)-6-chloropyridine (0.23 g, 0.70 mmol) from Example 92b in CH2Cl2 (5 mL) at 0° C. was treated with NEt3 (0.2 mL, 1.40 mmol) and methyl chloroformate (0.061 mL, 0.80 mmol). The mixture was allowed to warm to room temperature and stir for 1 h. The volatile components were evaporated and the residue was chromatographed (silica gel; MeOH/CH2Cl2, 1:19) to afford the title compound as a yellow oil (0.22 g, 82%). 1H NMR (CDCl3, 300 MHz) δ 1.42 (s, 9H), 2.28-2.35 (m, 2H), 3.71 (s, 3H), 3.89 (t, J=7.5 Hz, 2H), 4.10 (dd, J=3.0, 10.0 Hz, 1H), 4.36 (m, 1H), 4.40 (d, J=6.5 Hz, 2H), 4.54 (m, 1H), 7.35 (d, J=3.5 Hz, 1H), 8.01 (d, J=3.0 Hz, 1H); MS (CI/NH3) m/z 386 (M+H)+.

Workup

  1. customThe volatile components were evaporated
  2. customthe residue was chromatographed (silica gel; MeOH/CH2Cl2, 1:19)

Sources & evidence

ORD record
ord-6350cc41e8964662abe657d86b0471a4
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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