Benzyl 2-hydroxyacetate → 2-(Benzyloxy)-2-oxoethyl 3-(2-tert.-butoxy-2-oxoethyl)-4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 421807Notes

Reaction equation

HRID 421807 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:13](=[O:23])[N:12]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[C:11]([CH3:34])=[C:10]2[C:35](N2C=CN=C2)=[O:36])=[CH:5][CH:4]=1)#[N:2].[OH:42][CH2:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45]>>[C:19]([O:18][C:16](=[O:17])[CH2:15][N:14]1[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[C:10]([C:35]([O:42][CH2:43][C:44]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:45])=[O:36])=[C:11]([CH3:34])[N:12]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=2)[C:13]1=[O:23])([CH3:20])([CH3:21])[CH3:22]

Participants

3

Reactant 2

HCID 561337Benzyl 2-hydroxyacetateHCID 59684795tert.-Butyl [6-(4-cyanophenyl)-5-(1H-imidazol-1-ylcarbonyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]acetate

Product 1

HCID 596848532-(Benzyloxy)-2-oxoethyl 3-(2-tert.-butoxy-2-oxoethyl)-4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylateYield 32%

Procedure

The title compound is synthesized in analogy to Example 64 from Example 15A using benzyl hydroxyacetate instead of tert.-butyl-N-hydroxyethyl carbamate.

Sources & evidence

ORD record
ord-f30cf32509394f2799f9f20a89f9159d
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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