Benzylamine → HCID 131722113, compound

HRID 366096Notes

Reaction equation

HRID 366096 reaction equation
[C:1]([N:11]([C:45]([C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])=[N:46]SC)[CH2:12][CH2:13][CH2:14][C@H:15]([C:32]([NH:34][C@@H:35]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[CH3:36])=[O:33])[NH:16][C:17](=[O:31])[CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:59]([NH2:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>CN(C=O)C>[C:1]([N:11]([C:45]([C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])=[N:46][NH:66][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH2:12][CH2:13][CH2:14][C@H:15]([C:32]([NH:34][C@@H:35]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[CH3:36])=[O:33])[NH:16][C:17](=[O:31])[CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 131722109HCID 131722109, compound

Product 1

HCID 131722113HCID 131722113, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-N5 -(Cbz)-N5 -[methylthio(Cbz-iminomethyl)]-N2 -(diphenylacetyl)-(R)-N-[1-(4-methoxyphenyl)ethyl]ornithine amide (0.25 g, 0.312 mmol; see Example 35(d) above) and benzylamine (0.05 mL; 0.476 mmol) in DMF (5 mL) was stirred overnight at room temperature. The DMF was removed in vacuo and the residue dissolved in EtOAc. The EtOAc solution was washed with KHSO4 solution, 0.5 N NaOH solution and brine, dried over Na2SO4 and concentrated in vacuo to afford 0.25 g of the sub-title compound. The material was used directly in the next step.

Workup

  1. customThe DMF was removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe EtOAc solution was washed with KHSO4 solution, 0.5 N NaOH solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d960b9ae69548429567f5f165639b68
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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