2-Acetamidothiazole → HCID 13578788, compound

HRID 980228Notes

Reaction equation

HRID 980228 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:9])[CH3:8].C([Li])CCC.[O:15]=[C:16]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([F:29])([F:28])[F:27])[C:20]=2[N:19]=[C:18]([C@@H:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:31][CH3:32])[O:17]1>CCCCCC.O1CCCC1>[O:15]=[C:16]([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([F:29])([F:28])[F:27])[C:20]=1[NH:19][C:18](=[O:17])[C@@H:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH2:31][CH3:32])[CH2:8][C:7](=[O:9])[NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 176252-AcetamidothiazoleHCID 13578779HCID 13578779, compoundHCID 178418339Butyllithium

Product 1

HCID 13578788HCID 13578788, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Using the procedure of Step B of Example 3, 7.78 g of N-(2-thiazolyl)-acetamide, 240 ml of tetrahydrofuran and 78.3 ml of a solution of n-butyllithium in hexane and 10.2 g of the product of Step A in 75 ml of tetrahydrofuran were reacted to obtain 8.3 g of 1,1-dimethylethyl N-[(S) 2-[[2-[1,3-dioxo-3-(1,1-dimethylethyl N-[(S) 2-[[2-[1,3-dioxo-3-(2-thiazolylamino)-propyl]-6-(trifluoromethyl)-phenyl]-amino]-1-ethyl-2-oxoethyl]-carbamate melting at 190° C. and having a specific rotation of [α]D =-36.5°±2° (c=0.5% in CH3COOH).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-fdcbfe2858db43dba7c0024bd5f11f8f
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

Loading…