Dicyclohexylcarbodiimide → HCID 59680788, compound

HRID 2243830Notes

Reaction equation

HRID 2243830 reaction equation
[CH2:1]([O:10][C:11](=[O:24])[C@H:12]([C@@H:21]([CH3:23])[OH:22])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[CH2:25]([O:32][C:33]([N:35]([CH3:49])[C@H:36]([C:46](O)=[O:47])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:10][C:11](=[O:24])[C@H:12]([C@@H:21]([CH3:23])[O:22][C:46](=[O:47])[C@H:36]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)[N:35]([C:33]([O:32][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:34])[CH3:49])[NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11099982HCID 11099982, compoundHCID 14308410HCID 14308410, compound

Product 1

HCID 59680788HCID 59680788, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of D3 (33.72 g, 100 mmol) in DCM at 0° C., DMAP (3.66 g, 30 mmol), and E1 (34.33 g, 100 mmol) were added. After stirring 10 min at 0° C., DCC (22.7 g, 110 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred overnight. Then the mixture was filtered and the filtrate concentrated to dryness. The residue was chased with ACN (100 ml), filtered again and the filtrate was concentrated. The residue was dissolved in EtOAc (200 ml) and partitioned successively between aq KHSO4 (100 ml, 10%), aq NaHCO3 (100 ml, sat.) and brine (100 ml). The organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by flash LC (silica gel, grad EtOAc-Hex 1:4 to 1:2) to yield D2 (65.5 g, 98%). [α]D22−39.56 (c 1.06 CHCl3); Rf=0.55 (EtOAc:Hex 1:1).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. filtrationThen the mixture was filtered
  4. concentrationthe filtrate concentrated to dryness
  5. filtrationfiltered again
  6. concentrationthe filtrate was concentrated
  7. dissolutionThe residue was dissolved in EtOAc (200 ml)
  8. custompartitioned successively between aq KHSO4 (100 ml, 10%), aq NaHCO3 (100 ml, sat.) and brine (100 ml)
  9. dry with materialThe organic phase was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by flash LC (silica gel, grad EtOAc-Hex 1:4 to 1:2)

Sources & evidence

ORD record
ord-01806673c131439f99f55d4f3089a1cb
Source dataset
uspto-grants-2010_03
Patent number
US07678765B2

Reaction notes

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