L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- → methyl t-butyloxycarbonyl-O-benzyl-L-threonyl-D-isoglutaminate

HRID 1164383Notes

Reaction equation

HRID 1164383 reaction equation
C(OC([NH:8][C@@H:9]([C:16](=[O:18])[NH2:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=O)(C)(C)C.[C:19]([O:23][C:24]([NH:26][C@H:27]([C:38]([OH:40])=O)[C@@H:28]([CH3:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([NH:26][C@H:27]([C:38]([NH:8][C@@H:9]([C:16](=[O:18])[NH2:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:40])[C@@H:28]([CH3:37])[O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:25])([CH3:20])([CH3:21])[CH3:22]

Participants

3

Reactant 2

HCID 1549483L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 13190122Methyl t-butyloxycarbonyl-D-isoglutaminate

Product 1

HCID 70529565methyl t-butyloxycarbonyl-O-benzyl-L-threonyl-D-isoglutaminateYield 64.7%

Procedure

Methyl t-butyloxycarbonyl-D-isoglutaminate (0.65 g, 2.5 mmol) and t-butyloxycarbonyl-O-benzyl-L-threonine (0.77 g, 2.5 mmol) were reacted by the similar procedure to that described in Example 44 (I) to obtain methyl t-butyloxycarbonyl-O-benzyl-L-threonyl-D-isoglutaminate (0.73 g). m.p. 131°-132° C. [α]D22 +7.0° (C 0.5, ethanol). Rf3 =0.39, Rf5 =0.46.

Sources & evidence

ORD record
ord-30ab7e6f073f4f2eb4ea26d2abb70b0d
Source dataset
uspto-grants-1983_01
Patent number
US04369178

Reaction notes

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