Dicyclohexylcarbodiimide → HCID 9986121, compound

HRID 403183Notes

Reaction equation

HRID 403183 reaction equation
[C:1]([N:5]([C:23](=[O:32])[C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[CH:25]=1)[NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[O:14][C:13]=2[C:21]=1[CH3:22])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F:33][C:34]1[C:39](O)=[C:38]([F:41])[C:37]([F:42])=[C:36]([F:43])[C:35]=1[F:44].C1CCC(N=C=NC2CCCCC2)CC1>C(OCC)(=O)C>[F:33][C:34]1[C:39]([O:19][C:18]([CH:15]2[O:14][C:13]3[C:21]([CH3:22])=[C:9]([C:7]([NH:6][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:23](=[O:32])[C:24]4[CH:25]=[C:26]([CH3:31])[CH:27]=[C:28]([CH3:30])[CH:29]=4)=[O:8])[CH:10]=[CH:11][C:12]=3[O:17][CH2:16]2)=[O:20])=[C:38]([F:41])[C:37]([F:42])=[C:36]([F:43])[C:35]=1[F:44]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 10478412HCID 10478412, compound

Product 1

HCID 9986121HCID 9986121, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a vial, 97 mg (0.32 mm) of 7-[N′-tert-butyl-N′-(3,5-dimethyl-benzoyl)-hydrazinocarbonyl]-8-methyl-2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid, 60 mg (0.35 mm) of pentafluorophenol, 60 mg (0.32 mm) of DCC and 3 mL of ethyl acetate were stirred at room temperature for 24 hours. The reaction mixture was transferred to a round bottom flask and evaporated to dryness. The residue was redissolved in CH2Cl2 and chromatographed on silica gel. Elution with 40% ethyl acetate in hexane yielded the pentafluorophenol ester, 7-[N′-tert-butyl-N′-(3,5-dimethyl-benzoyl)-hydrazinocarbonyl]-8-methyl-2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid pentafluorophenyl ester, in a quantity of 80 mg. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.60 (d, 1H), 7.03 (s, 2H), 6.95 (d, 1H), 6.6 (q, 1H), 6.3 and 6.0 (d+d, 1H), 4.6 (m, 1H), 4.4 (m, 1H), 2.251 and 2.230 (s+s, 6H), 2.052 and 1.903 (s+s, 3H), 1.58 and 1.574 (s+s, 9H) (many signals split); TLC: Rf=0.52 (1:1 hexane:ethyl acetate).

Workup

  1. customThe reaction mixture was transferred to a round bottom flask
  2. customevaporated to dryness
  3. dissolutionThe residue was redissolved in CH2Cl2
  4. customchromatographed on silica gel
  5. washElution with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3e2f3c2e6016495da82a78e35f4d8f05
Source dataset
uspto-grants-2014_06
Patent number
US08748125B2

Reaction notes

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