Benzyloxycarbonyl-L-phenylalanine → HCID 22876169, compound

HRID 1376427Notes

Reaction equation

HRID 1376427 reaction equation
C(N([CH:7]([CH3:9])[CH3:8])C(C)C)C.C(OC([NH:20][C@H:21]([C:29]([OH:31])=O)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O)C1C=CC=CC=1.Cl.[CH3:33][NH:34][O:35][CH3:36].ON=C(C#N)[C:40]([O:42][CH2:43]C)=[O:41].[B-](F)(F)(F)F.CCO[C:55]([C:57]([C:67]#N)=NOC(N(C)C)=[N+](C)C)=O>CN(C=O)C>[CH3:36][O:35][N:34]([CH3:33])[C:29](=[O:31])[C@H:21]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=1[C:40]([O:42][CH2:43][C:8]1[CH:7]=[CH:9][CH:67]=[CH:57][CH:55]=1)=[O:41])[NH2:20]

Participants

7

Reactant 5

HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 22876169HCID 22876169, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

31.8 ml (0.18 mol) of N-ethyldiisopropylamine are added dropwise, at 0° C., to a solution of 17.94 g (0.06 mol) of benzyloxycarbonylphenylalanine, 5.97 g (0.06 mol) of N,O-dimethylhydroxylamine hydrochloride, 8.79 g (0.06 mol) of ethyl hydroxyiminocyanoacetate and 19.68 g (0.06 mol) of TOTU in 120 ml of DMF. The mixture is stirred at 0° C. for 1 h and at RT for 3 h. The solvent is removed by rotary evaporation i.V. and the residue is taken up in ethyl acetate; the solution thus obtained is washed several times with a 10% solution of citric acid, with a 10% solution of KHCO3 and with a saturated solution of NaCl. Once the solution has been dried over Na2SO4 and filtered, and the filtrate has been concentrated, 13.95 g (68%) of an oil remain.

Workup

  1. customThe solvent is removed by rotary evaporation i.V
  2. customthe solution thus obtained
  3. washis washed several times with a 10% solution of citric acid
  4. dry with materialOnce the solution has been dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate has been concentrated

Sources & evidence

ORD record
ord-9248da4855484db2aebaa4431fc3727d
Source dataset
uspto-grants-1997_09
Patent number
US05663139

Reaction notes

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