Water → Z-D-Dap-OH

HRID 1862521Notes

Reaction equation

HRID 1862521 reaction equation
C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(#[N:18])C.O.[CH2:20]([O:27][C:28]([NH:30][C@H:31]([CH2:35]C(N)=O)[C:32]([OH:34])=[O:33])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[CH2:20]([O:27][C:28]([NH:30][C@@H:31]([C:32]([OH:34])=[O:33])[CH2:35][NH2:18])=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 1712147N-Cbz-D-AsparagineHCID 12217721Iodo benzene diacetate

Product 1

HCID 6950592Z-D-Dap-OH

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred solution of iodobenzene diacetate (7.26 g) in a mixture of ethyl acetate (44 ml), acetonitrile (44 ml) and water (22 ml) was added 2(R)-benzyloxycarbonylamino-succinamic acid (5.0 g) at ambient temperature. After stirred for 3 hours, the reaction mixture was cooled to 5° C., followed by stirring for 2 hours. Insoluble material was collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give 2(R)-benzyloxycarbonylamino-β-alanine (4.15 g) as a white solid.

Workup

  1. stirringby stirring for 2 hours
  2. filtrationInsoluble material was collected by filtration
  3. washwashed with ethyl acetate
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-caef429ac5654e6cb5b66ed43a41e2bd
Source dataset
uspto-grants-2003_03
Patent number
US06538007B1

Reaction notes

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