Dichloromethane → HCID 131722107, compound

HRID 366092Notes

Reaction equation

HRID 366092 reaction equation
[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]([NH:10][C@@H:11]([C:16]([NH:18][C@@H:19]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[CH3:20])=[O:17])[CH2:12][CH2:13][CH2:14][NH2:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:34]([N:42]=[C:43]=[S:44])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH2:45](Cl)Cl>>[C:34]([NH:42][C:43]([NH:15][CH2:14][CH2:13][CH2:12][C@H:11]([C:16]([NH:18][C@@H:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:45])=[CH:23][CH:22]=1)[CH3:20])=[O:17])[NH:10][C:8](=[O:9])[CH:7]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[S:44])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 68284Benzoyl isothiocyanateHCID 131722032HCID 131722032, compound

Product 1

HCID 131722107HCID 131722107, compoundYield 83%

Procedure

To a solution of (R)-N2 -(diphenylacetyl)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide (2.0 g; 4.35 mmol; see Example 4(e) above) in CH2Cl2 (50 mL) was added benzoylisothiocyanate (0.59 mL; 4.35 mmol). The reaction mixture was stirred for 24 h at room temperature. The reaction was then concentrated in vacuo and the residue dissolved in EtOAc. The precipitated product, produced by addition of Et2O to the EtOAc solution, was collected and dried to afford 2.25 g (83%) of the sub-title compound as a white solid. The resultant material was used without further characterization.

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. customThe precipitated product, produced by addition of Et2O to the EtOAc solution
  4. customwas collected
  5. customdried

Sources & evidence

ORD record
ord-101b6d864b2b453884785ecab8b5b3f5
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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