Dicyclohexylcarbodiimide → HCID 69544498, compound

HRID 480324Notes

Reaction equation

HRID 480324 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH:13][CH2:14][C:15]2[CH:24]=[CH:23][C:18]3[O:19][CH2:20][CH2:21][O:22][C:17]=3[CH:16]=2)=[CH:8][CH:9]=1)=[O:4].C1CCC(N=C=NC2CCCCC2)CC1.[CH:40]1([C:43](O)=[O:44])[CH2:42][CH2:41]1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][N:13]([C:43]([CH:40]2[CH2:42][CH2:41]2)=[O:44])[CH2:14][C:15]2[CH:24]=[CH:23][C:18]3[O:19][CH2:20][CH2:21][O:22][C:17]=3[CH:16]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 15655Cyclopropanecarboxylic acidHCID 53885930HCID 53885930, compound

Product 1

HCID 69544498HCID 69544498, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-{3-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amino]-propyl}-thiophene-2-carboxylic acid methyl ester (0.435 g, 0.125 mmol), DCC (0.0284 g 0.137 mmol) and cyclopropanecarboxylic acid (0.0119 g, 0.137 mmol) in 10 mL CH2Cl2 was stirred at room temperature for 16 h. The mixture was filtered and the mother liquor was concentrated in vacuo. The residue was dissolved in 15 mL EtOAc and was filtered. The organic solution was washed with water followed by brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound of Step B as an oil (53 mg). MS 416 (M+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe mother liquor was concentrated in vacuo
  3. dissolutionThe residue was dissolved in 15 mL EtOAc
  4. filtrationwas filtered
  5. washThe organic solution was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4d5ececee534f10b9eefe6baa539393
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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