Glutamic acid diethyl ester → diethyl (2S)-2-[(4-iodobenzoyl)amino]pentanedioate

HRID 704869

Reaction equation

HRID 704869 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C@H:12]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C@H:12]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 73961Glutamic acid diethyl esterHCID 743734-Iodobenzoyl chloride

Product 1

HCID 1885228diethyl (2S)-2-[(4-iodobenzoyl)amino]pentanedioateYield 56%

Procedure

Diethyl N-(4-iodobenzoyl)-L-glutamate is prepared from 4-iodobenzoyl chloride and diethyl L-glutamate in 56% yield by the same method. m.p. 105°-106° C.; NMR (CDCl3, 300 MHz) delta 1.26 (t, 3H, J=7.2 Hz), 1.33 (t, 3H, J=7.2 Hz), 2.11-2.60 (m, 4H), 4.14 (q, 2H, J=7.2 Hz), 4.78 (m, 1H), 7.15 (d, 1H, J=7.2 Hz), 7.58 (d, 2H, J=8.4 Hz), 7.83 (d, 2H, J=8.4 Hz).

Sources & evidence

ORD record
ord-ee7be04b4b0742a08a38dd61b1545025
Source dataset
uspto-grants-1991_01
Patent number
US04988813

Linked notes

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