Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Oxalic Acid | HCID 971 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 3-Bromo-1-propanol | HCID 12308 | — |
| Reactant | 2-Dimethylaminopyridine | HCID 21885 | — |
| Reactant | (trans,trans)-4'-Pentyl-(1,1'-bicyclohexyl)-4-carboxylic acid | HCID 1712164 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59289083 | HCID 59289083 | — |
Reaction Steps
A solution of DCC (11.3 g, 54.5 mmol) in DCM is added slowly to an ice cooled mixture of 4′-pentyl-bicyclohexyl-4-carboxylic acid (15.0 g, 53.5 mmol), dimethylaminopyridine (1.1 g) and 3-bromopropan-1-ol (7.5 g, 54.0 mmol) and DCM (100 ml). After addition is complete, the mixture is stirred at 25° C. overnight. Oxalic acid is added to mop up excess DCC, the mixture is filtered and then evaporated to dryness to afford 4′-pentyl-bicyclohexyl-4-carboxylic acid 3-bromo-propyl ester as a white solid which gave correct mass ion by GCMS (M+401). 1H NMR gave expected signals. The product is used without further purification in the preparation of preferred example 2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08372307B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-c8c82968d4f0472795470d44c8d51669 |
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| Source note | uspto-grants-2013_02 |
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