3-Amino-2,2-dimethylpropanamide → HCID 66645907, compound

HRID 1694916Notes

Reaction equation

HRID 1694916 reaction equation
[NH2:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([NH2:6])=[O:5].OC1C=CC=CN=1.[CH3:16][C:17]1([CH3:55])[CH2:22][N:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[C:20](=[O:30])[CH2:19][N:18]1[CH2:31][C@H:32]([NH:42][S:43]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[N+:52]([O-:54])=[O:53])(=[O:45])=[O:44])[C@@H:33]1[CH2:37][C@@H:36]([CH:38]([CH3:40])[CH3:39])[C:35](=[O:41])[O:34]1>C(N(CC)CC)C>[C:4]([C:3]([CH3:8])([CH3:7])[CH2:2][NH:1][C:35](=[O:41])[C@H:36]([CH:38]([CH3:39])[CH3:40])[CH2:37][C@H:33]([OH:34])[C@@H:32]([NH:42][S:43]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[N+:52]([O-:54])=[O:53])(=[O:44])=[O:45])[CH2:31][N:18]1[CH2:19][C:20](=[O:30])[N:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:22][C:17]1([CH3:55])[CH3:16])(=[O:5])[NH2:6]

Participants

5

Reactant 3

HCID 111593153-Amino-2,2-dimethylpropanamideHCID 66645817HCID 66645817, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 66645907HCID 66645907, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

223 mg of 3-amino-2,2-di(methyl)propionamide obtained in Reference Example 2 (1.92 mmol) and 61 mg of 2-hydroxypyridine (0.64 mmol) were added to a solution of 367 mg of N-{(S)-2-[2,2-dimethyl-4-(2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide obtained in the above reaction (0.64 mmol) in triethylamine (6 ml), and the mixture was stirred at 80° C. for one hour. The reaction mixture was cooled and then concentrated under reduced pressure and further stirred at 80° C. for 14 hours. The reaction mixture was cooled and then water was added, followed by extraction with methylene chloride. Then, the organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=20/1) to obtain 345 mg of (2S,4S,5S)-6-[2,2-dimethyl-4-(2-methylphenyl)-5-oxopiperazin-1-yl]-4-hydroxy-2-isopropyl-5-(2-nitrobenzenesulfonylamino)hexanoic acid (2-carbamoyl-2-methylpropyl)amide (yield: 78%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. stirringfurther stirred at 80° C. for 14 hours
  4. temperatureThe reaction mixture was cooled
  5. additionwater was added
  6. extractionfollowed by extraction with methylene chloride
  7. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-4c5e1f52783b4643be7e6fb9e11aadd3
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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