Diisopropylethylamine → (2S,3S)-2-(tert-butoxycarbonyl-amino)-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide

HRID 650981Notes

Reaction equation

HRID 650981 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:13]([CH3:16])[CH2:14][CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:37][CH2:38][NH2:39])[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:37][CH2:38][NH:39][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C@@H:13]([CH3:16])[CH2:14][CH3:15])[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 217101572-[3-Methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethylamine

Product 1

HCID 56999350(2S,3S)-2-(tert-butoxycarbonyl-amino)-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

13.9 g of (2S,3S)-2-(tert-butoxycarbonyl-amino)-3-methyl-valeric acid (BOC-L-isoleucine) and 18.5 g of 2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethylamine are stirred at room temperature for two hours together with 25 g of (benzotriazol-1-yl)-tris(dimethylamino)-phosphonium hexafluorophosphate and 155 ml of diisopropylethylamine in 300 ml of dimethylformamide. The reaction mixture is then introduced into 800 ml of water. Extraction is carried out twice using 800 ml of ethyl acetate each time. The organic phases are washed twice using 250 ml of 2N hydrochloric acid each time, twice using 250 ml of 2N potassium hydrogen carbonate solution each time and once with 200 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated, yielding (2S,3S)-2-(tert-butoxy-carbonyl-amino)-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide in the form of a yellowish oil, which can be purified by chromatography on silica gel.

Workup

  1. extractionExtraction
  2. washThe organic phases are washed twice
  3. dry with materialonce with 200 ml of saturated sodium chloride solution, dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b10de14882b41e79e7933f65303978a
Source dataset
uspto-grants-2001_08
Patent number
US06277849B1

Reaction notes

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