Dicyclohexylcarbodiimide → HCID 131727406, compound

HRID 2110594Notes

Reaction equation

HRID 2110594 reaction equation
[CH3:1][CH:2]([CH3:22])[CH2:3][CH2:4][C:5]1([O:17][CH2:18][C:19]([OH:21])=[O:20])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[CH2:7][C:6]1=[O:16].[CH:23]1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.CO>[CH3:23][O:20][C:19](=[O:21])[CH2:18][O:17][C:5]1([CH2:4][CH2:3][CH:2]([CH3:22])[CH3:1])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[CH2:7][C:6]1=[O:16]

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 68843005HCID 68843005, compound

Product 1

HCID 131727406HCID 131727406, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 40B (20 mg, 0.066 mmol), 1,3-dicyclohexylcarbodiimide (20 mg, 0.1 mmol) in tetrahydrofuran (2 mL) and methanol (0.5 mL) was stirred at 25° C. for 16 hours. The solution was and concentrated in vacuo. Column chromatography on silica (7% methanol/dichloromethane) afforded the title compound (19 mg, 91%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.37-0.47 (m, 1H), 0.68 (dd, J=13.24, 6.62 Hz, 6H), 0.76-0.91 (m, 1H), 1.15-1.34 (m, 1H), 1.81-1.98 (m, 1H), 2.05-2.22 (m, 1H), 3.40 (d, J=15.08 Hz, 1H), 3.57 (s, 3H), 3.76 (d, J=15.07 Hz, 1H), 5.75 (s, 1H), 7.43-7.57 (m, 1H), 7.55-7.70 (m, 2H), 7.89 (d, J=7.72 Hz, 1H), 11.94 (br. s, 1H); MS (ESI) m/z 319.0 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f07d4180b387453694016bb558998033
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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