Dimethylcarbamoyl Chloride → tert-Butyl 2-(3-Methoxycarbonyladamant-1-ylcarbonylamino)-5-(N,N-dimethylaminocarbonyl)pent-4-ynoate

HRID 991763Notes

Reaction equation

HRID 991763 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([NH:17][CH:18]([CH2:26][C:27]#[CH:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].CCN(CC)CC.[CH3:36][N:37]([CH3:41])[C:38](Cl)=[O:39]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([NH:17][CH:18]([CH2:26][C:27]#[C:28][C:38]([N:37]([CH3:41])[CH3:36])=[O:39])[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 21940505tert-Butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)pent-4-ynoate

Product 1

HCID 21940493tert-Butyl 2-(3-Methoxycarbonyladamant-1-ylcarbonylamino)-5-(N,N-dimethylaminocarbonyl)pent-4-ynoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound from Step A of Example 49 (0.389 g, 1 mmol) was dissolved in dry DMF (5 mL) with dichlorobis(diphenylphosphine)palladium (II) (0.02 eq), Cul (0.02eq), Et3N (0.4 eq, 3 mL), and N,N-dimethylcarbamyl chloride (1.0 eq, 92 μL). The reaction mixture was stirred overnight at room temperature and then at 70° C. for 1 hour. The mixture was filtered through a pad of Celite and the solvent removed under reduced pressure. The crude product was purified by column chromatography (silica gel; EtOAc/hexanes, 2:3) to afford the title compound.

Workup

  1. waitat 70° C. for 1 hour
  2. filtrationThe mixture was filtered through a pad of Celite
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by column chromatography (silica gel; EtOAc/hexanes, 2:3)

Sources & evidence

ORD record
ord-3a628da6fb4549e19bb09eb81f09e651
Source dataset
uspto-grants-2002_10
Patent number
US06465513B1

Reaction notes

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