Glutamic acid diethyl ester → HCID 178508852, compound

HRID 1656567Notes

Reaction equation

HRID 1656567 reaction equation
N[C@H](C(OCC)=O)CCC(OCC)=O.[NH2:15][C:16]1[NH:21][C:20]2=[N:22][CH:23]=[C:24]([CH2:25][CH2:26][CH2:27][C:28]3[CH:49]=[CH:48][C:31]([C:32]([NH:34][C@H:35]([C:43]([O:45]CC)=[O:44])[CH2:36][CH2:37][C:38]([O:40]CC)=[O:39])=[O:33])=[CH:30][CH:29]=3)[C:19]2=[C:18]([OH:50])[N:17]=1>>[NH2:15][C:16]1[NH:21][C:20]2=[N:22][CH:23]=[C:24]([CH2:25][CH2:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([C:32]([NH:34][C@H:35]([C:43]([OH:45])=[O:44])[CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[O:33])=[CH:48][CH:49]=3)[C:19]2=[C:18]([OH:50])[N:17]=1

Participants

3

Reactant 2

HCID 73961Glutamic acid diethyl esterHCID 178471569HCID 178471569, compound

Product 1

HCID 178508852HCID 178508852, compound

Procedure

By substituting 4-(4-carbethoxyphenyl)butanal for 3-(4-carbethoxyphenyl)propanal in the procedure of Example 1 and thereafter substituting an equivalent amount of ethyl cyanoacetate for malononitrile in Example 2, there is obtained ethyl 4-[3-(2-amino-3-carbethoxyfur-4-yl)prop-1-yl]benzoate which thereafter is treated with guanidine in free base as described above to yield ethyl 4-[3-(2-amino-4-hydroxypyrrolo[2,3-d]-pyrimidin-5-yl)prop-1-yl]benzoate. This is subjected to saponification to yield 4-[3-(2-amino-4-hydroxypyrrolo[2,3-d]pyrimidin-5-yl)prop-1-yl]benzoic acid which then is coupled with diethyl L-glutamate, and the resulting diethyl N-[4-{3-(2-amino-4-hydroxypyrrolo[2,3-d]-pyrimidin-5-yl)prop-1-yl}benzoyl]-L-glutamate is saponified to yield N-[4-(3-(2-amino-4-hydroxypyrrolo[2,3-d]pyrimidin-5-yl)prop-1-yl}benzoyl]-L-glutamic acid, m.p. 190°-193° C.

Sources & evidence

ORD record
ord-fe43eac206aa45aca16b2fc000b6e8b3
Source dataset
uspto-grants-1993_10
Patent number
US05254687

Reaction notes

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