Diethyl N-(4-(N-((3,4-dihydro-4-oxo-3-((pivaloyl)oxy) methyl-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-L-glutamate → (S)-2-(2-fluoro-4-(((4-oxo-3,4-dihydroquinazolin-6-yl)methyl)(prop-2-ynyl)amino)benzamido)pentanedioic acid

HRID 2254573Notes

Reaction equation

HRID 2254573 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N:24]([CH2:45][C:46]#[CH:47])[CH2:25][C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[N:32]=[CH:31][N:30](COC(=O)C(C)(C)C)[C:29]3=[O:44])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][C@H:7]([C:15]([O:17]CC)=[O:16])[CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])=[O:5].O=C1C2C(=CC=C(CN(CC#C)C3C=CC(C(N[C@H](C(OCC)=O)CCC(OCC)=O)=O)=CC=3)C=2)N=CN1COC(=O)C(C)(C)C>>[F:1][C:2]1[CH:23]=[C:22]([N:24]([CH2:45][C:46]#[CH:47])[CH2:25][C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[N:32]=[CH:31][NH:30][C:29]3=[O:44])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5]

Participants

3

Reactant 2

HCID 13691215Diethyl N-(4-(N-((3,4-dihydro-4-oxo-3-((pivaloyl)oxy) methyl-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-L-glutamateHCID 14730576Diethyl N-(2-fluoro-4-(N-((3,4-dihydro-4-oxo-3((pivaloyl)oxy)methyl-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-L-glutamate

Product 1

HCID 136035435(S)-2-(2-fluoro-4-(((4-oxo-3,4-dihydroquinazolin-6-yl)methyl)(prop-2-ynyl)amino)benzamido)pentanedioic acid

Procedure

This compound was prepared from compound (10) in a similar manner to that for the preparation of CB 3804 from compound 5 in Example 1 using the reagent quantities and conditions set out in Table B.

Sources & evidence

ORD record
ord-8e6055fa44d6425ea2652da54e6f9419
Source dataset
uspto-grants-1993_08
Patent number
US05236927

Reaction notes

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