1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57889016, compound

HRID 1820289Notes

Reaction equation

HRID 1820289 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([O-:9])=O)[N:6]=1.[Na+].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:33][C@H:34]([CH:53]([CH3:55])[CH3:54])[C:35]([N:37]1[CH2:42][CH2:41][C@@:40]([C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=2)([OH:43])[C:39]([CH3:52])([CH3:51])[CH2:38]1)=[O:36]>CN(C=O)C>[NH2:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([NH:33][C@H:34]([CH:53]([CH3:55])[CH3:54])[C:35]([N:37]2[CH2:42][CH2:41][C@@:40]([C:44]3[CH:45]=[CH:46][C:47]([Cl:50])=[CH:48][CH:49]=3)([OH:43])[C:39]([CH3:51])([CH3:52])[CH2:38]2)=[O:36])=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 57888960HCID 57888960, compoundHCID 67299922HCID 67299922, compound

Product 1

HCID 57889016HCID 57889016, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium 2-aminooxazole-4-carboxylate (75 mg, 0.500 mmol), HOBt (67.5 mg, 0.500 mmol) and EDCI (96 mg, 0.500 mmol) were dissolved in DMF (0.5 mL). The mixture was stirred at rt for 0.5 h, then was added (R)-2-amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride (188 mg, 0.500 mmol) and further stirred for 2 h. The reaction was quenched with water and stirred at rt for 2 h. The solids were filtered and rinsed with water to give 2-amino-N—((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)oxazole-4-carboxamide (169 mg, 0.376 mmol, 75% yield).

Workup

  1. stirringfurther stirred for 2 h
  2. customThe reaction was quenched with water
  3. stirringstirred at rt for 2 h
  4. filtrationThe solids were filtered
  5. washrinsed with water

Sources & evidence

ORD record
ord-7116883ba95342bbba1455e6feef2421
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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