Boc-L-Valine → Ethyl 6-(((S)-2-((((S)-2-amino-3-methylbutanoyl)oxy)methyl)morpholino)methyl)-4-(2-bromo-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524783Notes

Reaction equation

HRID 524783 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][C@H:23]([CH2:27][OH:28])[CH2:22]2)[NH:12][C:11]([C:29]2[S:30][CH:31]=[CH:32][N:33]=2)=[N:10]1.C(OC([NH:41][C@@H:42]([CH:46]([CH3:48])[CH3:47])[C:43](O)=[O:44])=O)(C)(C)C>>[NH2:41][C@@H:42]([CH:46]([CH3:48])[CH3:47])[C:43]([O:28][CH2:27][C@@H:23]1[CH2:22][N:21]([CH2:20][C:13]2[NH:12][C:11]([C:29]3[S:30][CH:31]=[CH:32][N:33]=3)=[N:10][CH:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[Br:1])[C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:26][CH2:25][O:24]1)=[O:44]

Participants

3

Reactant 2

HCID 83693Boc-L-ValineHCID 118107582HCID 118107582, compound

Product 1

HCID 118107529Ethyl 6-(((S)-2-((((S)-2-amino-3-methylbutanoyl)oxy)methyl)morpholino)methyl)-4-(2-bromo-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 47%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(((S)-2-(hydroxymethyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (1 g, 1.9 mmol) was reacted with (S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanoic acid (0.63 g, 2.9 mmol) according to the procedure as described in Example 49 to give the title compound as a yellow solid (0.57 g, 47%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-caa79fde828c435ba21986fbbbd29d85
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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