Diisopropylethylamine → HCID 53892505、化合物

A mixture of (R)-3-amino-3-[4-(tert-butoxycarbonylamino)phenyl]-propanoic acid methyl ester [1.5 g, Reference Example 7(c)], mono-methyl glutarate (0.7 ml), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (2.05 g), diisopropylethylamine (1.8 ml) and dimethylformamide (40 ml) was stirred at ambient temperature for 18 hours. The reaction mixture was evaporated to dryness and diluted with water (75 ml) and the resultant mixture acidified to pH1.0 by addition of concentrated hydrochloric acid. The mixture was extracted twice with ethyl acetate (75 ml). The combined extracts were washed with water (75 ml) then dried over magnesium sulphate and then evaporated. The resulting waxy fawn solid (3.8 g) was dissolved in dichloromethane (20 ml), cooled to 0° C., and the solution treated with trifluoracetic acid (4 ml). After stirring at ambient temperature for 2 hours the reaction mixture was evaporated and the residue taken up in ethyl acetate (50 m). The resultant solution was treated with ice cold saturated aqueous potassium carbonate solution (20 ml) with stirring at ambient temperature for 5 minutes. The organic layer was separated, washed with water (30 ml), dried over magnesium sulphate, and then evaporated to give (R)3-(4-carboxybutanoyl-amino)-3-(4-aminophenyl)-propanoic acid methyl ester (1.32 g) as a yellow oil.

1. customThe reaction mixture was evaporated to dryness
2. additiondiluted with water (75 ml)
3. additionthe resultant mixture acidified to pH1.0 by addition of concentrated hydrochloric acid
4. extractionThe mixture was extracted twice with ethyl acetate (75 ml)
5. washThe combined extracts were washed with water (75 ml)
6. dry with materialthen dried over magnesium sulphate
7. customevaporated
8. dissolutionThe resulting waxy fawn solid (3.8 g) was dissolved in dichloromethane (20 ml)
9. temperaturecooled to 0° C.
10. additionthe solution treated with trifluoracetic acid (4 ml)
11. stirringAfter stirring at ambient temperature for 2 hours the reaction mixture
12. customwas evaporated
13. additionThe resultant solution was treated with ice cold saturated aqueous potassium carbonate solution (20 ml)
14. stirringwith stirring at ambient temperature for 5 minutes
15. customThe organic layer was separated
16. washwashed with water (30 ml)
17. dry with materialdried over magnesium sulphate
18. customevaporated

ORDレコード

ord-4837db99369646b68f7335635c553617

出典データセット

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06479519B1