Acetone → HCID 87299913, compound

HRID 1045061Notes

Reaction equation

HRID 1045061 reaction equation
[CH2:1]1[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3]C1C(O)=O.[Li]C.[CH3:15][C:16]([CH3:18])=[O:17].C1CNC(=O)C1.[Br:25][Br-]Br>CO>[Br:25][CH2:15][C:16]([CH:18]1[CH2:1][CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3]1)=[O:17]

Participants

5

Reactant 3

HCID 180Acetone2×HCID 12691896HCID 12691896, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 87299913HCID 87299913, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Octahydro-indene-2-carboxylic acid (490 mg, 2.92 mmol) was treated with MeLi following a method analogous to General Procedure A1 to produce the corresponding methyl ketone. The methyl ketone in MeOH was then treated with pyrrolidone hydrotribromide following a method analogous to General Procedure B1 to produce 2-bromo-1-(octahydro-inden-2-yl)-ethanone (600 mg, 84% overall crude yield). The above obtained bromoketone (150 mg, 0.61 mmol) was treated with 3-[1-(5-methyl-thiophen-2-ylmethyl)-thioureido]-propionic acid tert-butyl ester (150 mg) following a method analogous to General Procedure C to produce the aminothiazole propionic acid ester: 3-{(5-methyl-thiophen-2-ylmethyl)-[4-(octahydro-inden-2-yl)-thiazol-2-yl]-amino}-propionic acid tert-butyl ester.

Sources & evidence

ORD record
ord-d20ee118ce594d45ad272f300f90fcd6
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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