Dicyclohexylcarbodiimide → HCID 57950562, compound

HRID 598905Notes

Reaction equation

HRID 598905 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][C:25]1([CH3:33])[O:30][C:29](=[O:31])[CH2:28][C:27](=[O:32])[O:26]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:24][C:25]1([CH3:33])[O:30][C:29](=[O:31])[CH:28]([C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][C:14]2[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)[C:27](=[O:32])[O:26]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 57950747N-(tert-Butoxycarbonyl)-3-[6-(trifluoromethyl)pyridin-3-yl]-L-alanine

Product 1

HCID 57950562HCID 57950562, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(S)-2-(tert-Butoxycarbonylamino)-3-(6-(trifluoromethyl)pyridin-3-yl)propanoic acid (2.4 g, 7.2 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (1.1 g, 7.9 mmol), and N,N-dimethylpyridin-4-amine (1.4 g, 11 mmol) in 30 mL DCM were cooled in an ice-water-sodium chloride bath (−5° C.). N-((cyclohexylimino)methylene)cyclohexanamine (1.6 g, 7.9 mmol) in 50 mL DCM was added dropwise in about 40 minutes. The reaction mixture was stirred for 16 hours at room temperature. The suspension was filtered, and the solid was washed with DCM. The filtrate was washed with 5% KHSO4 (4×50 mL) and once with brine, and dried over MgSO4. After removing the solvent, the product was obtained as a white solid (3.0 g, 91%). LCMS (API-ES) m/z (%): 461.0 (100%, M+H+).

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with DCM
  3. washThe filtrate was washed with 5% KHSO4 (4×50 mL) and once with brine
  4. dry with materialdried over MgSO4
  5. customAfter removing the solvent

Sources & evidence

ORD record
ord-d59f076c738c485b903d043cc8ce13ce
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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