D-Aspartic Acid → (R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

HRID 431806

Reaction equation

HRID 431806 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@@H](C(O)=O)CC(O)=O.[K+].[Br-]>CO>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C:17](=[O:18])[O:19][C:14](=[O:16])[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 83887D-Aspartic AcidHCID 253877Potassium BromideHCID 5289152(2R)-2-(((benzyloxy)carbonyl)amino)butanedioic acid

Product 1

HCID 12416472(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamateYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(Benzyloxycarbonyl)-D-aspartic anhydride (25) is prepared from N-(benzyloxycarbonyl)-D-aspartic acid (24) by the method of McGarvey et al. (G. J. McGarvey et al., J. Amer. Chem. Soc., 1986, 108, 4943) with an overall yield of 80% with respect to D-aspartic acid (D-23). The melting point is 126-127° C. [α]D+26° (c 1.22, MeOH). Infrared (KBr): 1529, 1697 (O—CO—N), 1781 and 1866 (anhydride).

Sources & evidence

ORD record
ord-031121235b564c0bbb4e867ab7adb240
Source dataset
uspto-grants-2003_12
Patent number
US06660769B1

Linked notes

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