Methyl chloroformate → HCID 25193124, compound

HRID 1028471Notes

Reaction equation

HRID 1028471 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([NH2:21])[CH3:20])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.Cl[C:34]([O:36][CH3:37])=[O:35]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([NH:21][C:34](=[O:35])[O:36][CH3:37])[CH3:20])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 69189942HCID 69189942, compound

Product 1

HCID 25193124HCID 25193124, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 11D ((110 mg, 0.337 mmol) and diisopropylethylamine (0.5 mL) in methylene chloride (1 mL) cooled to 0° C. was added methyl chloroformate (67 μL, 0.76 mmol, 2.3 eq.). The mixture was stirred at room temperature overnight. The reaction mixture was purified directly on silica gel eluting with an ethyl acetate/hexane gradient (0-30%) to give the title compound (112 mg, 86%). 1H NMR (300 MHz, CDCl3) δ ppm 7.35-7.45 (m, 3 H), 7.27-7.33 (m, 2 H), 7.21-7.26 (m, 2 H), 6.91-7.01 (m, 2 H), 4.73-498 (m, 1 H), 3.83 (s, 3 H), 3.66 (s, 3 H); 1.47 (d, J=6.62 Hz, 3 H) MS (DCI): m/e 385 (M+H).

Workup

  1. customThe reaction mixture was purified directly on silica gel eluting with an ethyl acetate/hexane gradient (0-30%)

Sources & evidence

ORD record
ord-aa047e43032d4ddaa6b7da4f84967742
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

Loading…