Methyl chloroformate → HCID 68576719, compound

HRID 1865304Notes

Reaction equation

HRID 1865304 reaction equation
Cl.O1CCOCC1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH:21]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:22][CH2:23][N:24]2[CH2:31][CH:30]3[CH:26]([CH2:27][N:28]([C:32]([C:34]4[C:35]([CH3:41])=[N:36][CH:37]=[N:38][C:39]=4[CH3:40])=[O:33])[CH2:29]3)[CH2:25]2)[CH2:17][CH2:16]1)=[O:14])(C)(C)C.ClC(OC)=O>C(Cl)Cl>[CH3:8][O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH:21]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:22][CH2:23][N:24]2[CH2:25][CH:26]3[CH:30]([CH2:29][N:28]([C:32]([C:34]4[C:35]([CH3:41])=[N:36][CH:37]=[N:38][C:39]=4[CH3:40])=[O:33])[CH2:27]3)[CH2:31]2)[CH2:17][CH2:16]1)=[O:14]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 204431481,4-Dioxane hydrochlorideHCID 68584820HCID 68584820, compound

Product 1

HCID 68576719HCID 68576719, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl-dioxane (1 mL, 4.0 M) was added to 78a (Ar1=Ph, Ar2=4,6-dimethyl-pyrimidin-5-yl, 40 mg, 0.073 mmol). The mixture was stirred at RT for 90 min. The solvent was removed, and the residue was dried in vacuo. Methyl chloroformate (8 μL, 0.10 mmol) was added to a solution of the residue from the deprotection, TEA (16 μL, 0.11 mmol) in DCM (0.5 mL) maintained at 0° C. The reaction mixture was stirred and warmed to RT. The crude product was purified on a preparative TLC plate developed with a 45:55 mixture of DCM and DCM/MeOH/NH4OH (60/10/1) to afford 0.004 g (11%) of V-7.

Workup

  1. customThe solvent was removed
  2. customthe residue was dried in vacuo
  3. temperaturemaintained at 0° C
  4. stirringThe reaction mixture was stirred
  5. temperaturewarmed to RT
  6. customThe crude product was purified on a preparative TLC plate
  7. additiondeveloped with a 45:55 mixture of DCM and DCM/MeOH/NH4OH (60/10/1)
  8. customto afford 0.004 g (11%) of V-7

Sources & evidence

ORD record
ord-d3a63a15323149fb9d3aca3b00608bf6
Source dataset
uspto-grants-2009_12
Patent number
US07625905B2

Reaction notes

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