(2-Methoxyethoxy)acetic acid → HCID 69536205, compound

A mixture of (R)-3-amino-3-[4-(tert-butoxycarbonylamino)phenyl]-propanoic acid methyl ester [0.75 g, Reference Example 7(c)], 2-(2-methoxyethoxy)acetic acid (0.3 ml), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.02 g), diisopropylethylamine (0.9 ml) and dimethylformamide (25 ml) was stirred at ambient temperature 2 hours. The reaction mixture was poured into water (150 ml) and the resultant solid collected. The resulting fawn solid (1.5 g) was dissolved in dichloromethane (15 ml) and the solution was treated with trifluoracetic acid (3 ml). After stirring at ambient temperature for 2 hours the reaction mixture was evaporated. The residue was treated with toluene (50 ml), concentrated to dryness and the resultant material treated with ethyl acetate (50 ml). The resultant suspension was treated with saturated aqueous potassium carbonate solution (20 ml) with stirring at ambient temperature for 5 minutes. The organic layer was separated, dried over magnesium sulphate, and then evaporated to give the title compound (0.5 g) as a yellow oil.

1. customthe resultant solid collected
2. dissolutionThe resulting fawn solid (1.5 g) was dissolved in dichloromethane (15 ml)
3. additionthe solution was treated with trifluoracetic acid (3 ml)
4. stirringAfter stirring at ambient temperature for 2 hours the reaction mixture
5. customwas evaporated
6. additionThe residue was treated with toluene (50 ml)
7. concentrationconcentrated to dryness
8. additionthe resultant material treated with ethyl acetate (50 ml)
9. additionThe resultant suspension was treated with saturated aqueous potassium carbonate solution (20 ml)
10. stirringwith stirring at ambient temperature for 5 minutes
11. customThe organic layer was separated
12. dry with materialdried over magnesium sulphate
13. customevaporated

ORD record

ord-db2293e690314206aa2758b8ff93c509

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06479519B1