Oxalic Acid → HCID 59289083, compound

HRID 386325Notes

Reaction equation

HRID 386325 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[CH2:16]([CH:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]2)[CH2:23][CH2:22]1)[CH2:17][CH2:18][CH2:19][CH3:20].CN(C1C=CC=CN=1)C.[Br:45][CH2:46][CH2:47][CH2:48]O.C(O)(=O)C(O)=O>C(Cl)Cl>[Br:45][CH2:46][CH2:47][CH2:48][O:34][C:33]([CH:30]1[CH2:29][CH2:28][CH:27]([CH:24]2[CH2:25][CH2:26][CH:21]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][CH2:23]2)[CH2:32][CH2:31]1)=[O:35]

Participants

7

Reactant 5

HCID 971Oxalic AcidHCID 10868Dicyclohexylcarbodiimide2×HCID 123083-Bromo-1-propanolHCID 218852-DimethylaminopyridineHCID 1712164(trans,trans)-4'-Pentyl-(1,1'-bicyclohexyl)-4-carboxylic acid

Product 1

HCID 59289083HCID 59289083, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

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.

Workup

  1. temperaturecooled
  2. additionAfter addition
  3. filtrationthe mixture is filtered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-c8c82968d4f0472795470d44c8d51669
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

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