Diisopropylethylamine → (S)-benzyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-4-oxopyrrolidine-2-carboxylate

HRID 1751537Notes

Reaction equation

HRID 1751537 reaction equation
Cl.[O:2]=[C:3]1[CH2:7][NH:6][C@H:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4]1.[CH3:18][O:19][C:20]([NH:22][C@@H:23]([CH:27]([CH3:29])[CH3:28])[C:24](O)=[O:25])=[O:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:18][O:19][C:20]([NH:22][C@@H:23]([CH:27]([CH3:29])[CH3:28])[C:24]([N:6]1[CH2:7][C:3](=[O:2])[CH2:4][C@H:5]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:25])=[O:21]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 86648889HCID 86648889, compound

Product 1

HCID 59610664(S)-benzyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-4-oxopyrrolidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-Benzyl 4-oxopyrrolidine-2-carboxylate hydrochloride (1.92 g, 8.8 mmol), the acid (in this case (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid) (1.84 g, 10.56 mmol) and HATU (5.02 g, 13.2 mmol) were weighed out in a round bottom flask and dissolved in anhydrous DMF (44 mL). To this mixture was added DIPEA (6.82 g, 52.8 mmol) at room temperature and the mixture was stirred for 2 h. The crude mixture was diluted with EtOAc and washed respectively with brine, 10% Na2CO3 and brine again, and the mixture was dried over MgSO4, after filtration the mixture was concentrated down on rotovap. The residue was then purified on normal phase chromatography. (2.45 g, 74%).

Workup

  1. washwashed respectively with brine, 10% Na2CO3 and brine again
  2. dry with materialthe mixture was dried over MgSO4
  3. filtrationafter filtration the mixture
  4. concentrationwas concentrated down on rotovap
  5. customThe residue was then purified on normal phase chromatography

Sources & evidence

ORD record
ord-016791b0d2ba468a9df88eea53375f88
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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