Diisopropylethylamine → (S)-4-Methyl-2-[methyl-(3-methyl-but-2-enyl)-amino]-pentanoic acid

HRID 1069447Notes

Reaction equation

HRID 1069447 reaction equation
[CH3:1][N:2]([C:11](OC(C)(C)C)=O)[C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].CN(C(ON1N=NC2C=C[CH:31]=[CH:32][C:27]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:42](N(C(C)C)CC)(C)C>CC#N>[CH3:7][CH:5]([CH3:6])[CH2:4][C@H:3]([N:2]([CH3:1])[CH2:11][CH:42]=[C:32]([CH3:31])[CH3:27])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7010555(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acid

Product 1

HCID 86757058(S)-4-Methyl-2-[methyl-(3-methyl-but-2-enyl)-amino]-pentanoic acidYield 340.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Ia (0.535 g, 1.65 mmol), N-Methyl-N-Boc-L-Leucine (0.405 g, 1.65 mmol), HBTU (0.625 g, 1.65 mmol), and diisopropylethylamine (0.516 g, 6.6 mmol) was stirred in CH3CN (30 mL) for 15 hours. The reaction mixture was concentrated, redissolved in EtOAc, washed 3 times with saturated sodium bicarbonate solution and once with brine, then concentrated to give 1.2 g of the desired product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionredissolved in EtOAc
  3. washwashed 3 times with saturated sodium bicarbonate solution
  4. concentrationonce with brine, then concentrated

Sources & evidence

ORD record
ord-c752f89a232f4a87b821ba16bcddcadc
Source dataset
uspto-grants-2001_06
Patent number
US06251918B1

Reaction notes

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