tert-Butyl 2-bromo-2-methylpropionate → 2-(2-t-Butoxycarbonylprop-2-yloxyimino)-2-(thien-2-yl)acetic acid

HRID 614440Notes

Reaction equation

HRID 614440 reaction equation
[OH:1][N:2]=[C:3]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[C:4]([OH:6])=[O:5].Br[C:13]([CH3:22])([CH3:21])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C([NH2+]CCC1C=CC=CC=1)C1C=CC=CC=1>C(O)C>[C:17]([O:16][C:14]([C:13]([O:1][N:2]=[C:3]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[C:4]([OH:6])=[O:5])([CH3:22])[CH3:21])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 1549262Benethamine(1+)HCID 736296442-Hydroxyimino(thien-2-yl)acetic acid

Product 1

HCID 543000392-(2-t-Butoxycarbonylprop-2-yloxyimino)-2-(thien-2-yl)acetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from 2-hydroxyimino-2-(thien-2-yl)acetic acid (syn isomer) and t-butyl 2-bromo-2-methylpropionate, in a similar manner to that described for Preparation 1, in 78% yield as a colourless oil, and was characterised as the N-benzyl-2-phenylethylammonium salt, m.p. 201.3°-201.9° (from ethanol).

Workup

  1. customdescribed for Preparation 1, in 78% yield as a colourless oil

Sources & evidence

ORD record
ord-2f0fb51db1684aecb32016f21778516f
Source dataset
uspto-grants-1979_03
Patent number
US04144393

Reaction notes

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