L-Glutamic acid, N-(4-(methylamino)benzoyl)-, 1,5-diethyl ester → Diethyl methotrexate

HRID 1415971Notes

Reaction equation

HRID 1415971 reaction equation
Br.Br[CH2:3][C:4]1[N:5]=[C:6]2[C:11](=[N:12][CH:13]=1)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]2[NH2:15].[CH3:16][NH:17][C:18]1[CH:39]=[CH:38][C:21]([C:22]([NH:24][C@H:25]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:23])=[CH:20][CH:19]=1>>[CH3:32][CH2:31][O:30][C:28]([CH2:27][CH2:26][C@H:25]([NH:24][C:22]([C:21]1[CH:38]=[CH:39][C:18]([N:17]([CH2:3][C:4]2[N:5]=[C:6]3[C:7]([NH2:15])=[N:8][C:9]([NH2:14])=[N:10][C:11]3=[N:12][CH:13]=2)[CH3:16])=[CH:19][CH:20]=1)=[O:23])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29]

Participants

3

Reactant 2

HCID 75413L-Glutamic acid, N-(4-(methylamino)benzoyl)-, 1,5-diethyl esterHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Product 1

HCID 94528Diethyl methotrexate

Procedure

reacting this 6-bromomethyl-2,4-diaminopteridine hydrobromide with diethyl N-[4-(N-methylamino)-benzoyl]glutamate to give diethyl methotrexate, and

Sources & evidence

ORD record
ord-c5b289f1dcab4fb8a4b9babb2c87a3a0
Source dataset
uspto-grants-1999_06
Patent number
US05910588

Reaction notes

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