Diisopropylcarbodiimide → HCID 178444547, compound

HRID 1582520Notes

Reaction equation

HRID 1582520 reaction equation
C(N=C=NC(C)C)(C)C.[CH3:10][Si:11]([CH3:36])([CH2:30][CH2:31][C:32]([F:35])([F:34])[F:33])[CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[N:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[N:21][CH:22]=1.[CH2:37]([C@H:42]1[CH2:47][CH2:46][C@H:45]([C:48](O)=[O:49])[CH2:44][CH2:43]1)[CH2:38][CH2:39][CH2:40][CH3:41].CN(C1C=CC=CN=1)C>C(OCC)(=O)C>[CH3:36][Si:11]([CH3:10])([CH2:30][CH2:31][C:32]([F:35])([F:33])[F:34])[CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[N:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:48]([C@H:45]3[CH2:46][CH2:47][C@H:42]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:43][CH2:44]3)=[O:49])=[CH:25][CH:24]=2)=[N:19][CH:18]=1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 218852-DimethylaminopyridineHCID 135744189HCID 135744189, compoundHCID 178444557HCID 178444557, compound

Product 1

HCID 178444547HCID 178444547, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of diisopropyl-carbodiimide (DIC) (0.0454 g, 0.360 mmol) in ethyl acetate (3.0 ml) was added dropwise to a stirred solution of compound 41 (0.119 g, 0.300 mmol), trans-4-pentylcyclohexanecarboxlic acid (0.0713 g, 0.369 mmol) and dimethylaminopyridine (DMAP) (3.66 mg, 0.03 mmol) in ethyl acetate (3.0 ml). The reaction mixture was stirred at room temperature for 24 h, the solvent removed in vacuo and the residues purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1)] to give a colorless solid, which recrystallized acetonitrile to yield colorless crystals.

Workup

  1. customthe solvent removed in vacuo
  2. customthe residues purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1)]
  3. customto give a colorless solid, which
  4. customrecrystallized acetonitrile
  5. customto yield colorless crystals

Sources & evidence

ORD record
ord-2a12c54a75ee4eaeaafedf368badd371
Source dataset
uspto-grants-2004_05
Patent number
US06737124B2

Reaction notes

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