HCID 68700374, compound → HCID 68698520, compound

HRID 629672Notes

Reaction equation

HRID 629672 reaction equation
C1C2C(COC([NH:18][C:19]3[CH:45]=[CH:44][C:22]([C:23]([NH:25][NH:26][C@H:27]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:24])=[C:21]([N+:46]([O-:48])=[O:47])[CH:20]=3)=O)C3C(=CC=CC=3)C=2C=CC=1>CN(C)C=O>[C:40]([O:39][C:37](=[O:38])[C@H:27]([CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:26][NH:25][C:23](=[O:24])[C:22]1[CH:44]=[CH:45][C:19]([NH2:18])=[CH:20][C:21]=1[N+:46]([O-:48])=[O:47])([CH3:42])([CH3:43])[CH3:41]

Participants

3

Reactant 1

HCID 68700374HCID 68700374, compound

Product 1

HCID 68698520HCID 68698520, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 10 g of di-tert-butyl N-(4-(((9H-fluorene-9-yl)methoxy)carbonylamino)-2-nitrobenzamido)-L-glutamate in 200 ml of N,N-dimethylformamide 1.34 ml pyrrolidine were added. The mixture was stirred for 30 min. at room temperature and then evaporated to dryness under vacuum. After addition of 200 ml of diisopropylether and stirring for 15 min., the resulting suspension was kept at 0° C. over night. The product was sucked-off, washed with 60 ml of diisopropylether and then dried under vacuum to give 4.3 g of N-(4-amino-2-nitrobenzamido)-L-glutamic acid di-tert.-butylester as yellow needles (HPLC, assay 99.7% area).

Workup

  1. additionwere added
  2. customevaporated to dryness under vacuum
  3. additionAfter addition of 200 ml of diisopropylether
  4. stirringstirring for 15 min.
  5. waitthe resulting suspension was kept at 0° C. over night
  6. washwashed with 60 ml of diisopropylether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-b548b7c70e0e459ea6cfc3d739dbe0a8
Source dataset
uspto-grants-2016_04
Patent number
US09315506B2

Reaction notes

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