Ethylamine → HCID 131722112, compound

HRID 366095Notes

Reaction equation

HRID 366095 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]([NH2:61])[CH3:60]>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:61][CH2:59][CH3:60])[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 6341EthylamineHCID 131722109HCID 131722109, compound

Product 1

HCID 131722112HCID 131722112, compoundYield 65.6%

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(0.5g; 0.63 mmol; from step (d) above) and ethylamine (70% wt. in water; 0.08 mL; 0.94 mmol) in DMF (10 mL) was stirred for 1 h at room temperature. The DMF was removed in vacuo and the residue dissolved in EtOAc. The EtOAc solution was washed with KHSO4 solution, then 0.5 N NaOH solution and then brine, dried over Na2SO4 and concentrated in vacuo to afford 0.33 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
  4. dry with material0.5 N NaOH solution and then brine, dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2dc4e1a4b44476d874769b3a5f79b8c
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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