Hydrochloric Acid → HCID 57026044, compound

HRID 1976992Notes

Reaction equation

HRID 1976992 reaction equation
[CH3:1][O:2][C:3](=[O:42])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24](=[O:25])[CH:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:22]([C:33](=[O:35])[CH3:34])[CH:21]2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:16][CH:15]=1)[NH:5][C:6](OC(C)(C)C)=[O:7].Cl.[Cl:44][C:45]1[CH:53]=[CH:52][CH:51]=[C:50]([CH3:54])[C:46]=1C(O)=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O1CCOCC1.CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:42])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[C:24](=[O:25])[CH:23]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:22]([C:33](=[O:35])[CH3:34])[CH:21]2[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[CH:18][CH:19]=1)[NH:5][C:6]([C:46]1[C:50]([CH3:54])=[CH:51][CH:52]=[CH:53][C:45]=1[Cl:44])=[O:7]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 888702-Chloro-6-methylbenzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23383928HCID 23383928, compound

Product 1

HCID 57026044HCID 57026044, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(3-acetyl-5-oxo-2-phenyl-4-phenylmethyl-1-imidazolidinyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester (Diastereomer 1) (415 mg, 0.7 mmol) was treated with 10 mL of 4N HCl in dioxane at room temperature for 2 hr. After removal of solvent, the residue was dried overnight under vacuum. The residue (241 mg, 0.471 mmol) was dissolved in DMF (4 mL) and was treated with 2-chloro-6methylbenzoic acid (105 mg, 0.617 mmol), HBTU (234 mg, 0.617 mmol) and DIEA (246 μL, 1.42 mmol) at room temperature for 4 hr. The mixture was diluted with 30 mL of ethyl acetate, the mixture was washed with 1N HCl, water and brine (8 mL each), After it was dried over MgSO4, the solvent was removed and the residue was filtered through silica gel eluting with ethyl acetate:hexane (4:1 ) to give 4-(3-acetyl-5-oxo-2-phenyl-4-phenylmethyl-1-imidazolidinyl)-N-[(2-chloro-6-methylphenyl)carbonyl]-L-phenylalanine methyl ester diastereomer 1.

Workup

  1. customAfter removal of solvent
  2. customthe residue was dried overnight under vacuum
  3. washthe mixture was washed with 1N HCl, water and brine (8 mL each)
  4. dry with materialAfter it was dried over MgSO4
  5. customthe solvent was removed
  6. filtrationthe residue was filtered through silica gel eluting with ethyl acetate:hexane (4:1 )

Sources & evidence

ORD record
ord-3f4aff2ff795456bbd969cd65603ae70
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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