2-Acetamidothiazole → HCID 54403787, compound

HRID 980236Notes

Reaction equation

HRID 980236 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[CH:8][N:9]=1)(=[O:3])[CH3:2].[C:10]1([CH2:16][C@H:17]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C:18]2[O:23][C:22](=[O:24])[C:21]3[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([F:32])([F:31])[F:30])[C:20]=3[N:19]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1.C([Li])CCC.CCCCCC>[O:24]=[C:22]([C:21]1[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([F:31])([F:32])[F:30])[C:20]=1[NH:19][C:18]([C@@H:17]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:23])[CH2:2][C:1](=[O:3])[NH:4][C:5]1[S:6][CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 2

HCID 176252-AcetamidothiazoleHCID 13578785HCID 13578785, compound

Product 1

HCID 54403787HCID 54403787, compoundYield 103%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 178418339ButyllithiumSolvent

Procedure

Using the procedure of Step B of Example 7, a solution of 9.09 g of 2-acetylaminothiazole in 280 ml of tetrahydrofuran, 91 ml of n-butyllithium in solution in hexane and 13.9 g of product of Step A in 100 ml of tetrahydrofuran were reacted to obtain 19 g of 1,1-dimethylethyl N-[(S) 1-[[2-[1,3-dioxo-3-(2-thiazolylamino)-propyl]-6-(trifluoromethyl)-phenyl]-amino-carbonyl]-2-(phenyl)-ethyl]-carbamate.

Sources & evidence

ORD record
ord-e2ab74fbb7b14844bb471f4a5344c702
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

Loading…