Phosgene → HCID 10863743, compound

HRID 850599Notes

Reaction equation

HRID 850599 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][C@@H:6]([C:24]1[CH:32]=[CH:31][C:27]2[CH2:28][CH2:29][O:30][C:26]=2[CH:25]=1)[NH:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[CH2:20][CH2:19][CH2:18][NH:17][C:16]=2[N:15]=1)[CH3:2].[C:34]([O-])([O-])=[O:35].[K+].[K+].C(Cl)(Cl)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][C@@H:6]([C:24]1[CH:32]=[CH:31][C:27]2[CH2:28][CH2:29][O:30][C:26]=2[CH:25]=1)[N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[CH2:20][CH2:19][CH2:18][NH:17][C:16]=3[N:15]=2)[C:34]1=[O:35])[CH3:2]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 11091658HCID 11091658, compound

Product 1

HCID 10863743HCID 10863743, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-11 (11.8 mmol), CH2Cl2 (3 mL) and 20% K2CO3 was added phosgene (1.93 M toluene, 6.7 ml, 13.0 mmol) dropwise over 20 minutes. After stirring for 30 minutes, the organic layer was separated and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 5-10% methanol/ethyl acetate) to give 2-12 as a yellow oil. TLC Rf =0.25 (silica, 70:20:10 chloroform/ethyl acetate/methanol) 1H NMR (300 MHz, CDCl3) δ 7.12 (d, J=7.6 Hz, 1H), 7.02 (d, J=7.3 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 6.70 (s, 1H), 6.34 (d, J=7.3 Hz, 1H), 5.46 (t, J=7.9 Hz, 1H), 4.74 (s, 1H), 4.55 (t, J=8.9 Hz,2H), 4.10 (q, J=7.3 Hz, 2H), 3.41 (m, 2H), 3.21 (m, 6H), 2.95 (m,3H), 2.67(t, J=6.1 Hz, 2H), 2.52 (t, J=7.6 Hz, 2H), 1.88 (m, 5H), 1.20 (t, J=7.3 Hz, 3H).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over MgSO4
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 5-10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-5f0afc4242bf46e28959715b1f779567
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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