Morpholine → HCID 22894830, compound

HRID 2180827Notes

Reaction equation

HRID 2180827 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C@H:14]([C:16]([OH:18])=O)[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:19][C@H:20]([C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26])[C@H:21]([CH2:23][CH3:24])[CH3:22].C(N[C@H](C(O)=O)[C@H](CC)C)(OC(C)(C)C)=O.N1CCOCC1>C(Cl)(Cl)Cl.CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:19][C@H:20]([C:25]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)=[O:26])[C@H:21]([CH2:23][CH3:24])[CH3:22])=[O:18])[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 22894947HCID 22894947, compoundHCID 53788870N-(3-Nitrophenylacetyl)-L-alanine

Product 1

HCID 22894830HCID 22894830, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using N-(3-nitrophenylacetyl)-L-alanine (from Example D 1 above) and 4-(L-isoleucinyl)morpholine (prepared from N-BOC-L-isoleucine (Aldrich) and morpholine (Aldrich) using General Procedure M, followed by removal of the BOC-group using General Procedure P), the title compound was prepared as a solid (mp=156-160° C.). The reaction was monitored by tlc (Rf=0.45 in 9:1 CHCl3/MeOH) and the product was purified by silica gel chromatography using 98:2 CHCl3/MeOH as the eluent.

Workup

  1. customfollowed by removal of the BOC-group
  2. customwas prepared as a solid (mp=156-160° C.)
  3. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-591d1b1f26954c7e91e58df5cade15f9
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

Loading…