Diisopropylethylamine → (S)-3-benzyloxycarbonylamino-1-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]pyrrolidine-2,5-dione

HRID 459772Notes

Reaction equation

HRID 459772 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([O:17][C:18]([NH:20][C@H:21]([C:26]([NH:28][C:29]1[CH:34]=[C:33]([CH2:35][C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39](=[O:46])[NH:38][N:37]=2)[CH:32]=[CH:31][C:30]=1[F:47])=[O:27])[CH2:22][C:23]([OH:25])=O)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CC(N(C)C)=O>[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[CH2:22][C:23](=[O:25])[N:28]([C:29]2[CH:34]=[C:33]([CH2:35][C:36]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:39](=[O:46])[NH:38][N:37]=3)[CH:32]=[CH:31][C:30]=2[F:47])[C:26]1=[O:27])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 58823962(S)-3-benzyloxycarbonylamino-N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]succinamic acid

Product 1

HCID 58823963(S)-3-benzyloxycarbonylamino-1-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]pyrrolidine-2,5-dioneYield 69.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

O-Benzotriazol-1-yl-N,N,N′N′-tetramethyluronium tetrafluoroborate (0.289 g, 0.9 mmol) and diisopropylethylamine (0.193 g, 1.5 mmol) were added sequentially to a stirred solution of (S)-3-benzyloxycarbonylamino-N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]succinamic acid (0.35 g, 0.68 mmol) in dimethylacetamide (3 ml), the mixture was stirred at ambient temperature for 24 hours, then it was added dropwise to stirred, ice-cold water (30 ml). The mixture was stirred for 1 hour, then the resulting solid was collected by filtration and dried in vacuo to give (S)-3-benzyloxycarbonylamino-1-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]pyrrolidine-2,5-dione (0.238 g) as an off white solid, m.pt. 121–127° C. (softens 102° C.); m/z (M+H)+. 501, 96% purity.

Workup

  1. additionit was added dropwise
  2. stirringto stirred
  3. stirringThe mixture was stirred for 1 hour
  4. filtrationthe resulting solid was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-aba67b767d724b3a8bd0dc51d0d26210
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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