Chlorosuccinimide → (2Z)-2-[5-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyiminoacetic acid

HRID 525917Notes

Reaction equation

HRID 525917 reaction equation
[C:1]([O:5][C:6](=[O:29])[C:7]([O:10]/[N:11]=[C:12](/[C:16]1[N:17]=[C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[S:19][CH:20]=1)\[C:13]([OH:15])=[O:14])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Cl:37])C(=O)C1>CN(C)C=O>[C:1]([O:5][C:6](=[O:29])[C:7]([O:10]/[N:11]=[C:12](/[C:16]1[N:17]=[C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[S:19][C:20]=1[Cl:37])\[C:13]([OH:15])=[O:14])([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 189632922-(((1-(tert-Butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid

Product 1

HCID 88534087(2Z)-2-[5-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyiminoacetic acidYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid (70 g, 147 mmol) and NCS (23.50 g, 176 mmol) in N,N-Dimethylformamide (DMF) (735 mL) was stirred at 40° C. for 2.5 h. The reaction was quenched by addition of H2O (2 L), EtOAc (1 L) and 5% aq. sodium thiosulfate soln (400 mL). The organic layer was separated, and washed with H2O (2×), brine, dried and evaporated to afford (Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)acetic acid (69 g, 91% purity, 135 mmol, 92% yield) as a light yellow foaming solid. LCMS: (M+H)+: 464.2

Workup

  1. customThe reaction was quenched by addition of H2O (2 L), EtOAc (1 L) and 5% aq. sodium thiosulfate soln (400 mL)
  2. customThe organic layer was separated
  3. washwashed with H2O (2×), brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-4e57ff6c26064c74828e4a2dad61b104
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

Loading…