Pyridine → Z-D-Dap-OH

HRID 1904160Notes

Reaction equation

HRID 1904160 reaction equation
FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.NC(=O)C[C@@H](NC(OCC1C=CC=CC=1)=O)C(O)=O.N1C=CC=CC=1.[NH2:47][CH2:48][C@@H:49]([NH:53][C:54]([O:56][C:57](=O)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:55])[C:50]([OH:52])=[O:51]>O.CN(C)C=O>[NH2:47][CH2:48][C@@H:49]([NH:53][C:54]([O:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:55])[C:50]([OH:52])=[O:51]

Participants

6

Reactant 4

HCID 1049PyridineHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 1712147N-Cbz-D-AsparagineHCID 54301764(R)-3-amino-2-[[(benzoyloxy)carbonyl]amino]propanoic acid

Product 1

HCID 6950592Z-D-Dap-OH

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

[Bis(trifluoroacetoxy)iodo]benzene (6.45 g., 15.0 mmole) is dissolved in water-dimethylformamide 1:1 (80 ml.) and (R)-4-amino-2-[[(benzyloxy)carbonyl]amino]-4-oxobutanoic acid (2.4 g., 9.0 mmole) is added over a 10 minute period. The reaction is allowed to stir at room temperature for 30 minutes, until dissolution occurs. Pyridine (1.62 ml., 20 mmole) is added dropwise over a 5 minute period. The reaction is allowed to stir for 3 hours then stripped of solvent to yield a yellow precipitate. This semi-solid is triturated with a combination of isopropanol:ethyl ether. The precipitate is filtered and dried over phosphorus pentoxide to yield 1.35 g. of (R)-3-amino-2-[[(benzoyloxy)carbonyl]amino]propanoic acid as a white solid.

Workup

  1. stirringto stir for 3 hours
  2. customto yield a yellow precipitate
  3. customThis semi-solid is triturated with a combination of isopropanol
  4. filtrationThe precipitate is filtered
  5. dry with materialdried over phosphorus pentoxide
  6. customto yield 1.35 g

Sources & evidence

ORD record
ord-fdc3ab8aeba74fec99f9d4459d634441
Source dataset
uspto-grants-1989_06
Patent number
USH0000642

Reaction notes

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