2-Acetamidothiazole → HCID 54338439, compound

HRID 980232Notes

Reaction equation

HRID 980232 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[CH:8][N:9]=1)(=[O:3])[CH3:2].C([Li])CCC.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][C@H:25]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:26]2[O:31][C:30](=[O:32])[C:29]3[CH:33]=[CH:34][CH:35]=[C:36]([C:37]([F:40])([F:39])[F:38])[C:28]=3[N:27]=2)=[CH:16]1>O1CCCC1.CCCCCC>[O:32]=[C:30]([C:29]1[CH:33]=[CH:34][CH:35]=[C:36]([C:37]([F:38])([F:39])[F:40])[C:28]=1[NH:27][C:26]([C@@H:25]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:46])([CH3:45])[CH3:47])[CH2:24][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:15][CH:16]=1)=[O:31])[CH2:2][C:1](=[O:3])[NH:4][C:5]1[S:6][CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 3

HCID 176252-AcetamidothiazoleHCID 13578783HCID 13578783, compoundHCID 178418339Butyllithium

Product 1

HCID 54338439HCID 54338439, compoundYield 106.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Using the procedure of Step B of Example 7, a solution of 18.34 g of 2-acetylaminothiazole in 565 ml of tetrahydrofuran, 184 ml of a solution of n-butyllithium in hexane and 20.3 g of the product of Step A in 150 ml of tetrahydrofuran were reacted to obtain 28 g of 1,1-dimethylethyl N-[(S) 1-[[2-[1,3-dioxo-3-(2-thiazolylamino)-propyl]-6-(trifluoromethyl)-phenyl]-aminocarbonyl]-2-(1H-indol-3-yl)-ethyl]-carbamate as an orange oil which was used as is in the following step.

Sources & evidence

ORD record
ord-46036baa3b4b4b7897105628e94bc87c
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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