Glutaric anhydride → Methyl (r) 4-[1-(1,2,3,4-tetrahydro-quinolin-6-yl)-2-methoxycarbonyl-ethylcarbamoyl]-butyrate

HRID 396722Notes

Reaction equation

HRID 396722 reaction equation
[NH2:1][C@@H:2]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12][CH2:11]2)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:25]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26]1.O1CCC[CH2:34]1>>[NH:14]1[C:15]2[C:10](=[CH:9][C:8]([C@H:2]([NH:1][C:29]([CH2:28][CH2:27][CH2:26][C:25]([O:31][CH3:34])=[O:32])=[O:30])[CH2:3][C:4]([O:6][CH3:7])=[O:5])=[CH:17][CH:16]=2)[CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 3

HCID 7940Glutaric anhydrideHCID 8028TetrahydrofuranHCID 69563649methyl (R) 3-amino-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate

Product 1

HCID 57297160Methyl (r) 4-[1-(1,2,3,4-tetrahydro-quinolin-6-yl)-2-methoxycarbonyl-ethylcarbamoyl]-butyrate

Procedure

A stirred solution of methyl (R) 3-amino-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate (1.7 g, Reference Example 14) in tetrahydrofuran (50 ml) was treated with glutaric anhydride. After stirring for 4 hours the mixture was evaporated to dryness the residue was dissolved in methanol (40 ml) and treated with conc. sulphuric acid (20 drops). This solution was stirred at reflux for 3 hours and then allowed to stand at room temperature overnight. After the addition of solid sodium bicarbonate (10 g) the mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The aqueous layer was extracted with fresh ethyl acetate. The combined organic layer and extracts were washed with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with ethyl acetate to give the title compound (1.6 g) as a yellow oil. MS (ES+) 363 (MH+), 385 (MNa+) MS (ES−) 361 (MH−).

Workup

  1. customwas evaporated to dryness the residue
  2. dissolutionwas dissolved in methanol (40 ml)
  3. additiontreated with conc. sulphuric acid (20 drops)
  4. stirringThis solution was stirred
  5. temperatureat reflux for 3 hours
  6. waitto stand at room temperature overnight
  7. additionAfter the addition of solid sodium bicarbonate (10 g) the mixture
  8. customwas evaporated to dryness
  9. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  10. extractionThe aqueous layer was extracted with fresh ethyl acetate
  11. washThe combined organic layer and extracts were washed with brine
  12. customdried
  13. customevaporated

Sources & evidence

ORD record
ord-0c3c5efc533c43d4a569aac283eeb837
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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