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Diisopropylethylamine → (R)-4,4-Dimethyl-2-(2-morpholin-4-yl-2-oxo-ethyl)-pentanoic acid {(S)-1-[(5-ethyl-1,2,4-oxadiazol-3-yl)-hydroxy-methyl]-propyl}-amide

HRID 1796167
Notes
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Reaction equation

HRID 1796167 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][C@H:4]([CH2:8][C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[C:5]([OH:7])=O.FC(F)(F)C(O)=O.[NH2:26][CH:27]([CH2:37][CH3:38])[C@@H:28]([C:30]1[N:34]=[C:33]([CH2:35][CH3:36])[O:32][N:31]=1)[OH:29].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH2:35]([C:33]1[O:32][N:31]=[C:30]([CH:28]([OH:29])[C@@H:27]([NH:26][C:5](=[O:7])[C@@H:4]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[CH2:3][C:2]([CH3:1])([CH3:18])[CH3:17])[CH2:37][CH3:38])[N:34]=1)[CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15975488(R)-4,4-Dimethyl-2-(2-morpholin-4-yl-2-oxo-ethyl)-pentanoic acidHCID 69427127(S)-2-amino-1-(5-ethyl-1,2,4-oxadiazol-3-yl)-butan-1-ol trifluoroacetate

Product 1

HCID 86588341
(R)-4,4-Dimethyl-2-(2-morpholin-4-yl-2-oxo-ethyl)-pentanoic acid {(S)-1-[(5-ethyl-1,2,4-oxadiazol-3-yl)-hydroxy-methyl]-propyl}-amide
Yield 83.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-4,4-Dimethyl-2-(2-morpholin-4-yl-2-oxo-ethyl)-pentanoic acid (200 mg, 0.778 mmol) in dimethylformamide (10 ml) was treated successively with (S)-2-Amino-1-(5-ethyl-1,2,4-oxadiazol-3-yl)-butan-1-ol; compound with trifluoro-acetic acid (233 mg, 0.779 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (296 mg, 0.779 mmol) and diisopropylethylamine (0.271 ml, 1.559 mmol). Reaction stirred at room temperature overnight. Solvent evaporated under reduced pressure. Residue taken up in ethyl acetate and washed with 1N hydrochloric acid, saturated aqueous bicarbonate solution and water, dried over Na2SO4 and solvent evaporated under reduced pressure to give (R)-4,4-Dimethyl-2-(2-morpholin-4-yl-2-oxo-ethyl)-pentanoic acid {(S)-1-[(5-ethyl-1,2,4-oxadiazol-3-yl)-hydroxy-methyl]-propyl}-amide as a yellow solid (277 mg).

Workup

  1. customReaction
  2. customSolvent evaporated under reduced pressure
  3. washwashed with 1N hydrochloric acid, saturated aqueous bicarbonate solution and water
  4. dry with materialdried over Na2SO4 and solvent
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-def2f061edab4703b7983b831c7818a3
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07030116B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes