Triethylamine → N-(Benzyloxycarbonyl)aspartic acid

HRID 1464223Notes

Reaction equation

HRID 1464223 reaction equation
C(N(CC)CC)C.C[O:9][C:10](=[O:37])[C@H:11]([CH2:33][C:34]([OH:36])=[O:35])[N:12]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>CO>[CH2:26]([O:25][C:23]([NH:12][C@@H:11]1[C:10](=[O:9])[O:37][C:34](=[O:36])[CH2:33]1)=[O:24])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1.[CH2:16]([O:15][C:13]([NH:12][C@H:11]([C:10]([OH:37])=[O:9])[CH2:33][C:34]([OH:36])=[O:35])=[O:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 53782664HCID 53782664, compound

Product 2

HCID 2723942N-(Benzyloxycarbonyl)aspartic acidHCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Suitable amount of sample was withdrawn from the uniform reaction mixture thus obtained and dissolved in a methanol solution containing 5% by weight of triethylamine. α- and β-Isomers of N-benzyloxycarbonylcarbobenzoxy-L-aspartic acid methyl ester formed by the reaction of N-benzyloxycarbonyl-L-aspartic anhydride with methanol and residual N-benzyloxycarbonyl-L aspartic acid were determined by high performance liquid chromatography. The content and yield of N-benzyloxycarbonyl-L-aspartic anhydride were calculated from measured values. Results are shown in Table 7.

Workup

  1. customSuitable amount of sample was withdrawn from the uniform reaction mixture
  2. customthus obtained

Sources & evidence

ORD record
ord-b571b9fb04e343a1b62e15c21c21b708
Source dataset
uspto-grants-1994_04
Patent number
US05302743

Reaction notes

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