HCID 67074477, compound → HCID 67074020, compound

HRID 2095511Notes

Reaction equation

HRID 2095511 reaction equation
COC(=O)[CH2:4][CH2:5][N:6]([C@H:18]([CH3:32])[CH2:19][N:20]([C:25](OC(C)(C)C)=[O:26])[CH2:21][CH2:22][CH2:23][OH:24])[C:7](=[O:17])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1>Cl.CO>[Cl:16][C:12]1[CH:11]=[C:10](/[CH:9]=[CH:8]/[C:7]([N:6]2[CH2:5][CH2:4][C:25](=[O:26])[N:20]([CH2:21][CH2:22][CH2:23][OH:24])[CH2:19][C@H:18]2[CH3:32])=[O:17])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 67074477HCID 67074477, compound

Product 1

HCID 67074020HCID 67074020, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

63.1 g (0.13 mol) of 3-{{(R)-2-[tert-butoxycarbonyl-(3-hydroxy-propyl)-amino]-1-methyl-ethyl}-[(E)-3-(3-chloro-phenyl)-acryloyl]-amino}-propionic acid methyl ester was dissolved in 130 ml of 4 N HCl in MeOH. The reaction was stirred for 4 h after which time it was evaporated to dryness and the residue redissolved in CH2Cl2, washed with sat. aq. NaHCO3, dried (Na2SO4) and the mixture concentrated to 300 ml. 3.6 g (0.03 mol) of 1,5,7-triazabucyclodec-5-ene was then added and the mixture stirred for 16 h after which time the solvent was evaporated. The residue was redissolved in 100 ml of MeOH and 6N NaOH was added until the pH was basic and the mixture stirred for 1 h. The solvent was evaporated, the residue redissolved in CH2Cl2, washed with 10% citric acid solution, washed with sat. aq. NaHCO3, dried (Na2SO4) and concentrated. This afforded the titled compound in 62% yield as a colorless foam. MS: 351.2 (MH+, Cl).

Workup

  1. customwas evaporated to dryness
  2. dissolutionthe residue redissolved in CH2Cl2
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationthe mixture concentrated to 300 ml
  6. stirringthe mixture stirred for 16 h after which time the solvent
  7. customwas evaporated
  8. dissolutionThe residue was redissolved in 100 ml of MeOH
  9. addition6N NaOH was added until the pH
  10. stirringthe mixture stirred for 1 h
  11. customThe solvent was evaporated
  12. dissolutionthe residue redissolved in CH2Cl2
  13. washwashed with 10% citric acid solution
  14. washwashed with sat. aq. NaHCO3
  15. dry with materialdried (Na2SO4)
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-161feb93ff6c417eb29128a49235ec04
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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