Acetonitrile → Z-Dap-OH

HRID 12410Notes

Reaction equation

HRID 12410 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13]C(=O)N)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.C(#[N:28])C.C(O)(=O)C.C(O)(=O)C.I(C1C=CC=CC=1)=O>O>[NH2:28][CH2:13][C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 75314Benzyloxycarbonyl-asparagineHCID 73357407Acetic acid;iodosylbenzene

Product 1

HCID 2756313Z-Dap-OH

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N-(benzyloxycarbonyl)-L-asparagine (7.5 g) were added ethyl acetate (36 ml), acetonitrile (36 ml), water (18 ml) and iodosobenzene diacetate (10 g), and the mixture was stirred overnight at room temperature. The reaction mixture was filtered, and the obtained solid was washed with ethyl acetate to give the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-4e5415304ca54750898b53f2b9270f2c
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Reaction notes

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