HCID 88615492, compound → HCID 10870340, compound

HRID 652824Notes

Reaction equation

HRID 652824 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:21]/[O:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])/[C:8]([O:10]CC2C=CC([N+]([O-])=O)=CC=2)=[O:9])[N:6]=1.[H][H]>O1CCCC1.[Pd]>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:21]/[O:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 2

HCID 88615492HCID 88615492, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10870340HCID 10870340, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

In 1.2 l of tetrahydrofuran is dissolved 20 g (45.9 mmol) of p-nitrobenzyl (Z)-2-(2-amino-4-thiazolyl)-2-(t-butoxycarbonylmethoxyimino)acetate and, after addition of 20 g of 10% palladium-on-carbon, hydrogen gas is bubbled into the solution. After completion of the reaction, the catalyst is filtered off, and the filtrate is poured into 300 ml of water. The mixture is adjusted to about pH 8 with 5% aqueous sodium bicarbonate and washed with three 200-ml portions of ethyl acetate. The aqueous layer is adjusted to pH about 2 with 10% HCl and cooled to 5° C. or lower. The resulting crystalline precipitate is collected by filtration, washed with water and dried under reduced pressure to give 11.1 g of (Z)-2-(2-amino-4-thiazolyl)-2-(t-butoxycarbonylmethoxyimino)acetic acid.

Workup

  1. customis bubbled into the solution
  2. customAfter completion of the reaction
  3. filtrationthe catalyst is filtered off
  4. additionthe filtrate is poured into 300 ml of water
  5. washwashed with three 200-ml portions of ethyl acetate
  6. filtrationThe resulting crystalline precipitate is collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-a917c52773b6491ea38dfb54da86704c
Source dataset
uspto-grants-1987_06
Patent number
US04673739

Reaction notes

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