Morpholine → 4[N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-(S)-2-amino-3-tert-butoxybutyryl]morpholine

HRID 2180826Notes

Reaction equation

HRID 2180826 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]([CH:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH3:30])[C:21]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22].C(N[C@H](C(O)=O)[C@@H](C)OC(C)(C)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]([CH:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[CH3:30])[C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])=[O:18])[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 7015770(2S,3R)-3-(tert-butoxy)-2-(((tert-butoxy)carbonyl)amino)butanoic acidHCID 53788870N-(3-Nitrophenylacetyl)-L-alanineHCID 696230294-((S)-2-amino-3-tert-butoxybutyryl]-morpholine

Product 1

HCID 696227954[N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-(S)-2-amino-3-tert-butoxybutyryl]morpholine

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using N-(3-nitrophenylacetyl)-L-alanine (from Example Dli above) and 4-[(S)-2-amino-3-tert-butoxybutyryl]-morpholine (prepared from N-BOC-O-ter-butyl-L-threonine (Sigma) 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. The reaction was monitored by tlc (Rf=0.1 in 95:5 CHCl3/MeOH) and the product was purified by silica gel chromatography using 96:4 CHCl3/MeOH as the eluent.

Workup

  1. customfollowed by removal of the BOC-group
  2. customwas prepared as a solid
  3. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f3482a08f0384761b9ed5e0c4f2ea2d4
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

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