Water → HCID 86760995, compound

HRID 1437643Notes

Reaction equation

HRID 1437643 reaction equation
Cl.[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)[CH2:19][CH2:18][NH:17][CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([NH:44][CH2:45][C:46](O)=[O:47])(OC(C)(C)C)=O.CCN=C=NCCCN(C)C.Cl.O>CN(C=O)C.CCN(CC)CC>[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:26]=[C:25]([C:33]([F:36])([F:34])[F:35])[CH:24]=2)[CH2:19][CH2:18][N:17]([C:46](=[O:47])[CH2:45][NH2:44])[CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86760996HCID 86760996, compound

Product 1

HCID 86760995HCID 86760995, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of the compound (31.8 mg) obtained in Example 25 in DMF (2.0 ml), Et3N (8.4 μl ) was added, Boc-glycine (21 mg) and WSC.HCl (23 mg) were added at room temperature and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and then the product was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% citric acid solution and saturated brine, and dried, and the solvent was evaporated under reduced pressure, and then the residue was purified by preparative HPLC. A 4 N hydrogen chloride/ethyl acetate solution was further added thereto, and the reaction mixture was stirred for 1 hour, and then the solvent was evaporated. The obtained residue was dissolved in ethyl acetate, washed with an aqueous saturated sodium hydrogen carbonate solution and brine, dried, and then the solvent was evaporated under reduced pressure to obtain the title compound.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous 10% citric acid solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative HPLC
  6. additionA 4 N hydrogen chloride/ethyl acetate solution was further added
  7. stirringthe reaction mixture was stirred for 1 hour
  8. customthe solvent was evaporated
  9. dissolutionThe obtained residue was dissolved in ethyl acetate
  10. washwashed with an aqueous saturated sodium hydrogen carbonate solution and brine
  11. customdried
  12. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59c84f1c92474b1ca596f5a1ebc30a2c
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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