Dichloromethane → HCID 131722109, compound

HRID 366094Notes

Reaction equation

HRID 366094 reaction equation
I.[CH3:2][S:3][N:4]=[CH:5][NH:6][CH2:7][CH2:8][CH2:9][C@H:10]([C:27]([NH:29][C@@H:30]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[CH3:31])=[O:28])[NH:11][C:12](=[O:26])[CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Cl)Cl.[CH:43]1[CH:48]=[CH:47][C:46]([CH2:49][O:50][C:51](Cl)=[O:52])=[CH:45][CH:44]=1.[C:54]([O-:57])([O-])=[O:55].[K+].[K+]>O>[C:51]([N:6]([C:5]([C:54]([O:57][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:55])=[N:4][S:3][CH3:2])[CH2:7][CH2:8][CH2:9][C@H:10]([C:27]([NH:29][C@@H:30]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[CH3:31])=[O:28])[NH:11][C:12](=[O:26])[CH:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([O:50][CH2:49][C:46]1[CH:47]=[CH:48][CH:43]=[CH:44][CH:45]=1)=[O:52]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 178490622HCID 178490622, compound

Product 1

HCID 131722109HCID 131722109, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-N5 -[Methylthio(iminomethyl)]-N2 -(diphenylacetyl)-(R)-N-[1-(4-methoxyphenyl)ethyl]ornithine amide hydroiodide (1.38 g; 2.09 mmol; from step (c) above), CH2Cl2 (100 mL), Cbz-Cl (0.75 mL; 5.22 mmol), water (100 mL) and K2CO3 (1.16 g; 8.36 mmol) were combined and stirred for 18 h at room temperature. The organic layer was separated and washed with KHSO4 solution (twice), NaHCO3 solution (twice) and brine (twice), dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica column eluting with hexanes:EtOAc (3:1). Fractions containing the desired product were combined and concentrated in vacuo to afford 0.65 g (39%) of the sub-title compound. The material was used without farther characterization.

Workup

  1. customThe organic layer was separated
  2. washwashed with KHSO4 solution (twice), NaHCO3 solution (twice) and brine (twice),
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica column
  6. washeluting with hexanes:EtOAc (3:1)
  7. additionFractions containing the desired product
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cce90769da8f4178891cee08e7bfe941
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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