Dicyclohexylcarbodiimide → HCID 25160788, compound

HRID 512927Notes

Reaction equation

HRID 512927 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:20](O)[CH2:21][CH2:22][C:23]4[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=4[C:25]([OH:27])=[O:26])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:20]4[O:27][C:25](=[O:26])[C:24]5[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=5[CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 19762414HCID 19762414, compound

Product 1

HCID 25160788HCID 25160788, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of hydroxy-acid 48 (24.0 g, 54.06 mmol) in dichloromethane (500 ml) was added 4-dimethylamino pyridine (13.23 g, 108 mmol) and stirred for 15 minutes. To the above mixture dicyclohexylcarbodiimide (14.53 g, 70.2 mmol) was added and stirred for 24 hours. The precipitated DCU was filtered off and the filtrate was concentrated. The residue obtained after concentration was suspended in THF (150 ml) and filtered to remove any residual DCU followed by washing the residue with additional THF (2×50 ml). The combined filtrate was concentrated in vacuo and subjected to FC. The residue obtained after concentration of the eluent was triturated with hexane (200 ml) and filtered to give solid lactone 49 (20.0 g, 80%).

Workup

  1. stirringstirred for 24 hours
  2. filtrationThe precipitated DCU was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue obtained
  5. concentrationafter concentration
  6. filtrationfiltered
  7. customto remove any residual DCU
  8. washby washing the residue with additional THF (2×50 ml)
  9. concentrationThe combined filtrate was concentrated in vacuo
  10. customThe residue obtained after concentration of the eluent
  11. customwas triturated with hexane (200 ml)
  12. filtrationfiltered

Sources & evidence

ORD record
ord-457c08de673b4077905ff22cf1b9f82b
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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