Dicyclohexylcarbodiimide → HCID 69516255, compound

HRID 458445Notes

Reaction equation

HRID 458445 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=O)[CH2:11][O:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[C:17]1([CH3:25])[O:24][C:22](=[O:23])[CH2:21][C:19](=O)O1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1.[C:50]([C:53]1[CH:60]=[CH:59][C:56](C=O)=[CH:55][CH:54]=1)([OH:52])=[O:51]>N1CCCCC1.C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13](=[O:15])/[C:21](/[C:22]([O:24][CH2:17][CH3:25])=[O:23])=[CH:19]/[C:56]2[CH:59]=[CH:60][C:53]([C:50]([OH:52])=[O:51])=[CH:54][CH:55]=2)[CH2:11][O:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 120884-Formylbenzoic acidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 218852-DimethylaminopyridineHCID 11009386HCID 11009386, compound

Product 1

HCID 69516255HCID 69516255, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To (4S)-3-(tert-butoxycarbonyl)-1,3-oxazolidine-4-carboxylic acid (11.15 g, 0.051 mol), Meldrum's acid (7.33 g, 0.051 mol), dimethylaminopyridine (12.44 g, 0.102 mol) and DCM (200 ml) was added 1,3-dicyclohexylcarbodiimide (10.52 g, 0.051 mol). After 24 h the reaction was filtered, extracted twice with 1N HCl (200 ml) once with water, dried (Na2SO4), filtered, concentrated, then warmed to reflux in 100% ethanol for 2 h. The reaction was concentrated to a pale yellow oil (14.3 g). A portion of this material (5.88 g, 0.02 mol) was refluxed 2 h using Dean Stark trap with 4-carboxybenzaldehyde (3.0 g, 0.02 mol), piperidine (110 mg, 0.0012 mol) and toluene (100 ml). The reaction was filtered, concentrated to give A as a yellow gum (7.1 g, 85%). LCMS m/z 420 (MH+).

Workup

  1. filtrationAfter 24 h the reaction was filtered
  2. extractionextracted twice with 1N HCl (200 ml) once with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperaturewarmed
  7. temperatureto reflux in 100% ethanol for 2 h
  8. concentrationThe reaction was concentrated to a pale yellow oil (14.3 g)
  9. filtrationThe reaction was filtered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9ab0e2c6129a4223a51b01f183daa98b
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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