Ethylmorpholine → Methyl 4-{3-[2-(3-bromobenzoylamino)ethoxy]-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl}pentanoate

HRID 1280869Notes

Reaction equation

HRID 1280869 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:21][CH:20]2[C:8]([CH3:33])([CH:9]3[CH:17]([CH:18]([OH:22])[CH2:19]2)[CH:16]2[C:12]([CH3:31])([CH:13]([CH:23]([CH3:30])[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:14][CH2:15]2)[CH:11]([OH:32])[CH2:10]3)[CH2:7][CH2:6]1.[Br:34][C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=1)[C:38](O)=[O:39].C(N1CCOCC1)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:34][C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=1)[C:38]([NH:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:21][CH:20]2[C:8]([CH3:33])([CH:9]3[CH:17]([CH:18]([OH:22])[CH2:19]2)[CH:16]2[C:12]([CH3:31])([CH:13]([CH:23]([CH3:30])[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:14][CH2:15]2)[CH:11]([OH:32])[CH2:10]3)[CH2:7][CH2:6]1)=[O:39]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 114563-Bromobenzoic acidHCID 516892Sodium BicarbonateHCID 18425132Methyl 4-[3-(2-aminoethoxy)-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl]pentanoate

Product 1

HCID 18425126Methyl 4-{3-[2-(3-bromobenzoylamino)ethoxy]-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl}pentanoateYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

932 mg of methyl 4-[3-(2-aminoethoxy)-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl]pentanoate (Example 1d) and 402 mg of 3-bromobenzoic acid are dissolved in 20 ml of anhydrous DMF and first 656 mg of O[(cyano(ethoxycarbonyl)methylene)amino]-1,1,3,3-tetramethyluronium tetrafluoroborate (TOTU) (Proceedings of the 21st European Peptide Symposium, Peptides 1990, Editors E. Giralt and D. Andreu, Escom, Leiden, 1991) and then 760 μL of N-ethylmorpholine are added at 0° C. The reaction mixture is stirred at RT for 20.5 hours and then poured into 100 ml of a 10% aqueous NaHCO3 solution. It is extracted 3 times using 150 ml of EA each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. Chromatography on silica gel using EA yields 610 mg of a viscous oil.

Workup

  1. extractionIt is extracted 3 times
  2. dry with materialThe extract is dried over Na2SO4
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-8c1b7468207f40aeadbc24ad6a395383
Source dataset
uspto-grants-2002_09
Patent number
US06451781B1

Reaction notes

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