Dicyclohexylcarbodiimide → HCID 86622989, compound

HRID 2233800Notes

Reaction equation

HRID 2233800 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:23]=[CH:22][C:17]2[O:18][C:19](=[O:21])[O:20][C:16]=2[CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][CH:25]([CH3:34])[C:26]([O:28][C@H:29]([CH3:33])[C@H:30](O)[CH3:31])=[O:27].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:23]=[CH:22][C:17]2[O:18][C:19](=[O:21])[O:20][C:16]=2[CH:15]=1)[C:10]([O:12][C@H:30]([CH3:31])[C@H:29]([O:28][C:26](=[O:27])[CH:25]([CH3:34])[CH3:24])[CH3:33])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 59296770HCID 59296770, compoundHCID 86622988HCID 86622988, compound

Product 1

HCID 86622989HCID 86622989, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of (2S)-2-[(tert-butoxy)carbonylamino]-3-(2-oxobenzo[3,4-d]1,3-dioxolen-5-yl)propanoic acid (16) (5.86 g, 18.1 mmol) and (1R,2R)-2-hydroxy-1-methylpropyl 2-methylpropanoate (15) (4.15 g, 21.84 mmol) in anhydrous dichloromethane (40 mL), a solution of dicyclohexylcarbodiimide (5.62 g, 27.3 mmol) in anhydrous dichloromethane (10 mL) was added dropwise at 0° C. To the solution, a catalytic amount of 4-(dimethylamino)pyridine was added. The resulting mixture was stirred at 0° C. for 30 min, then at room temperature for 2 hours. TLC indicated a completed reaction. The side product, dicyclohexylurea, was removed by filtration. The filtrate was diluted with dichloromethane (100 mL) and washed with 10% citric acid and water. The organic layer was collected, dried over MgSO4, and concentrated to provide the title compound (17) (6.4 g, 76% yield). MS (ESI) m/z 465.9 (M+H)+.

Workup

  1. waitat room temperature for 2 hours
  2. customa completed reaction
  3. customThe side product, dicyclohexylurea, was removed by filtration
  4. additionThe filtrate was diluted with dichloromethane (100 mL)
  5. washwashed with 10% citric acid and water
  6. customThe organic layer was collected
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5319d9efc7804fad9ceca5d73338cd3f
Source dataset
uspto-grants-2010_05
Patent number
US07709527B2

Reaction notes

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