Triethylamine → HCID 86759119, compound

HRID 396727Notes

Reaction equation

HRID 396727 reaction equation
C([NH:8][C@@H:9]([CH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH2:20][CH2:19][CH2:18]2)[C:10]([O:12][CH3:13])=[O:11])(OC(C)(C)C)=O.C(N(CC)CC)C.[Cl:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[C:34]=1[C:35](Cl)=[O:36]>O1CCCC1>[NH2:8][C@@H:9]([CH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:35](=[O:36])[C:34]1[C:33]([Cl:32])=[CH:41][CH:40]=[CH:39][C:38]=1[Cl:42])[CH2:20][CH2:19][CH2:18]2)[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 69563299methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1,2,3,4-tetrahydroquinolin-6-yl)propanoate

Product 1

HCID 86759119HCID 86759119, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of methyl (S) 2-(N-boc-amino)-3-(1,2,3,4-tetrahydro-quinolin-6-yl)-propionate [500 mg, Reference Example 19(a)] in tetrahydrofuran (20 ml) was treated successively with triethylamine (360 mg) and 2,6-dichlorobenzoyl chloride (380 mg). The mixture was stirred at 40° C. for 2 hours and then partitioned between ethyl acetate (100 ml) and dilute hydrochloric acid (100 ml). The organic phase was washed with sodium bicarbonate solution, then dried and then evaporated. The residue was dissolved in trifluoroacetic acid (2 ml) and the clear solution was left at room temperature for 30 minutes then evaporated. The residue was partitioned between ethyl acetate and dilute hydrochloric acid. The organic phase was washed with sodium bicarbonate solution, then dried and then evaporated to give the title compound (200 mg) as a colourless oil.

Workup

  1. custompartitioned between ethyl acetate (100 ml) and dilute hydrochloric acid (100 ml)
  2. washThe organic phase was washed with sodium bicarbonate solution
  3. customdried
  4. customevaporated
  5. dissolutionThe residue was dissolved in trifluoroacetic acid (2 ml)
  6. waitthe clear solution was left at room temperature for 30 minutes
  7. customthen evaporated
  8. customThe residue was partitioned between ethyl acetate and dilute hydrochloric acid
  9. washThe organic phase was washed with sodium bicarbonate solution
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-30153378a4124541a492bc0a763ddfd9
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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