Dicyclohexylcarbodiimide → HCID 21963999, compound

HRID 2212370Notes

Reaction equation

HRID 2212370 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])[CH2:16][CH2:15][CH:14]([CH2:17][S:18]([CH2:21][C:22](O)=[O:23])(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC1C(O)=C(F)C(F)=C(F)C=1F.C1([N:51]=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])[CH2:16][CH2:15][CH:14]([CH2:17][S:18]([CH2:21][C:22]([NH2:51])=[O:23])(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 21964008HCID 21964008, compound

Product 1

HCID 21963999HCID 21963999, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the product of Example 75 (100 mg, 0.2 mmol) in ethyl acetate (8 mL) was added pentafluorophenol (55 mg, 0.3 mmol). The solution was cooled to 0° C. and dicyclohexylcarbodiimide was added (62 mg, 0.3 mmol). After 2 h the reaction was filtered through Celite® and the filtrate concentrated to give a white solid (130 mg). This was dissolved in a 2 M solution of ammonia in methanol (10 ml) and heated to 50° C. in a sealed tube for 16 h. The mixture was concentrated and the residue purified by flash chromatography on silica eluting with dichloromethane/methanol (9:1) to give a white solid (45 mg).

Workup

  1. filtrationAfter 2 h the reaction was filtered through Celite®
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-7dc7dc7b3079486fa4c867e330b1294f
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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