Ethanol → (3R,10S)-5-Methyl-3-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid ethyl ester

HRID 965138Notes

Reaction equation

HRID 965138 reaction equation
[CH3:1][CH:2]([CH3:32])[CH2:3][C@@H:4]([C:9](=[O:31])[NH:10][C@H:11]1[CH2:28][C:27]2=[CH:29][N:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=32)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:30])[CH2:5][C:6]([OH:8])=[O:7].[CH2:33](O)[CH3:34].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH2:33]([O:7][C:6](=[O:8])[CH2:5][C@H:4]([C:9](=[O:31])[NH:10][C@H:11]1[CH2:28][C:27]2=[CH:29][N:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=32)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:30])[CH2:3][CH:2]([CH3:32])[CH3:1])[CH3:34]

Participants

5

Reactant 3

HCID 702EthanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 52893145-Methyl-3-(9-oxo-1,8-diaza-tricyclo(10.6.1.013,18)nonadeca-12(19),13,15,17-tetraen-10-ylcarbamoyl)-hexanoic acid

Product 1

HCID 67693720(3R,10S)-5-Methyl-3-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid ethyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(3R,10S)-5-Methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid (183 mg) was taken up in 40 mL of dry CH2Cl2 and at 0° C. ethanol (0.5 mL, 5 eq) was added followed by N,N-dimethylaminopyridine (0.1 eq, 5 mg) and finally EDCI (209 mg, 5 eq). The resulting solution was stirred from 0° C. to room temperature overnight. Additional CH2Cl2 (100 mL) was added and the mixture was washed with 0.5N HCl (2×50 mL), saturated NaHCO3 (2×50 mL) and finally with brine (1×50 mL). The organic layer was dried over Na2 SO4, filtered and evaporated to dryness. Recrystallization from ethyl acetate and petroleum ether gave (3R,10S)-5-Methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid ethyl ester as a white solid (Yield: 108 mg, 55%), MS: 470 (M+H)+.

Workup

  1. additionwas added
  2. washthe mixture was washed with 0.5N HCl (2×50 mL), saturated NaHCO3 (2×50 mL) and finally with brine (1×50 mL)
  3. customThe organic layer was dried over Na2 SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customRecrystallization from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-8b30e8f667f348e49763c347530d5c96
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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