Diisopropylethylamine → HCID 68379204, compound

HRID 2038784Notes

Reaction equation

HRID 2038784 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=O)[C@@H:10]([CH3:12])[OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Cl.[CH3:18][C:19]1[N:24]=[CH:23][C:22]([C:25]2[CH:26]=[N:27][C:28]([C@H:31]([NH2:33])[CH3:32])=[CH:29][CH:30]=2)=[CH:21][CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C1COCC1>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([C:13](=[O:15])[NH:33][C@@H:31]([C:28]1[N:27]=[CH:26][C:25]([C:22]2[CH:23]=[N:24][C:19]([CH3:18])=[CH:20][CH:21]=2)=[CH:30][CH:29]=1)[CH3:32])[C@H:10]([OH:11])[CH3:12])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724766N-tert-Butoxycarbonyl-L-threonineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68379230HCID 68379230, compound

Product 1

HCID 68379204HCID 68379204, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-Boc-(L)-threonine (0.13 g, 0.61 mmol), (R)-1-(6′-methyl-[3,3′]bipyridinyl-6-yl)-ethylamine dihydrochloride (0.16 g, 0.56 mmol) and HATU (0.23 g, 0.61 mmol) was added THF (1 mL) followed by diisopropylethylamine (0.48 mL, 2.8 mmol). After 2 h, the volatiles were removed under a stream of N2 and the resulting oil was purified by flash chromatography on silica gel (0→5% MeOH/CH2Cl2) yielding 250 mg of {(1S,2R)-2-hydroxy-1-[(R)-1-(6′-methyl-[3,3′]bipyridinyl-6-yl)-ethylcarbamoyl]-propyl}-carbamic acid tert-butyl ester as a tan solid, m/z 415.8 [M+H]+.

Workup

  1. customthe volatiles were removed under a stream of N2
  2. customthe resulting oil was purified by flash chromatography on silica gel (0→5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-90e61e7bc0a4461aa67903502278e668
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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