Methyl chloroformate → HCID 10411909, compound

HRID 1768480Notes

Reaction equation

HRID 1768480 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[F:17])[CH2:7][N:6]1[C:18]([N:20]([CH3:22])[CH3:21])=[O:19].C(N(CC)CC)C.Cl[C:37]([O:39][CH3:40])=[O:38]>C(Cl)Cl>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([F:17])=[C:10]([C:8]2[CH2:7][N:6]([C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[C:5]([CH2:4][CH2:3][CH2:2][NH:1][C:37](=[O:38])[O:39][CH3:40])([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:9]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 10001131HCID 10001131, compound

Product 1

HCID 10411909HCID 10411909, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 20 mg (0.05 mmol) of amine 20-2 in CH2Cl2 was added 21 μL (0.15 mmol) of triethylamine and 5.8 μL (0.10 mmol) of methyl chloroformate. After stirring overnight the reaction was partitioned between EtOAc and 10% KHSO4, the organic phase was washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 22-1 as a white solid. Data for 22-1: 1HNMR (500 MHz, d6-DMSO) δ 7.6 (m, 1H), 7.5-7.1 (m, 8H), 6.2 (s, 1H), 4.95 (m, 1H), 4.7 (m, 1H), 3.55 (s, 3H), 3.0 (m, 2H), 2.7 (s, 6H), 2.7-2.5 (m, 1H), 2.05 (m, 1H), 1.4 (m, 2H) ppm. HRMS (ES) calc'd M+H for C24H27ClFN3O3: 460.1798. Found: 460.1797.

Workup

  1. customwas partitioned between EtOAc and 10% KHSO4
  2. washthe organic phase was washed with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by column chromatography on silica gel with EtOAc/hexanes

Sources & evidence

ORD record
ord-e5e9f756c62e446cbc1eb46a6ef810ea
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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