Dicyclohexylcarbodiimide → HCID 69797268, compound

HRID 2180228Notes

Reaction equation

HRID 2180228 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:10]([OH:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:37]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=[O:40])[NH:38][NH2:39]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:10]([OH:14])[C:11]([NH:39][NH:38][C:37]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 79242Benzyl carbazateHCID 69588616HCID 69588616, compound

Product 1

HCID 69797268HCID 69797268, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 1C (1.10 g, 3.65 mmol) in dichloromethane at 0° C. was treated with dicyclohexylcarbodiimide (0.83 g, 4.02 mmol), stirred for 30 minutes, treated with benzyl carbazate (0.69 g, 4.02 mmol), warmed to room temperature, and stirred for 32 hours. The mixture was filtered, and concentrated, and the concentrate was purified by flash column chromatography on silica gel with ethyl acetate in hexanes to provide the desired product.

Workup

  1. stirringstirred for 32 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customthe concentrate was purified by flash column chromatography on silica gel with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6a0490fdc66d49409796c7824af53c0f
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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