Diisopropylethylamine → HCID 67606716, compound

HRID 1965213Notes

Reaction equation

HRID 1965213 reaction equation
[C:1]([N:8]([CH3:14])[C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:48]([O:55][C:56]([N:58]1[CH2:62][CH:61]([CH2:63][O:64][C:65]2[CH:70]=[CH:69][C:68]([F:71])=[C:67]([F:72])[CH:66]=2)[CH:60]2[N:73]([C:76](=[O:83])[CH:77]([NH2:82])[C:78]([CH3:81])([CH3:80])[CH3:79])[CH2:74][CH2:75][CH:59]12)=[O:57])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN1C(=O)CCC1.CCOC(C)=O>[CH2:48]([O:55][C:56]([N:58]1[CH2:62][CH:61]([CH2:63][O:64][C:65]2[CH:70]=[CH:69][C:68]([F:71])=[C:67]([F:72])[CH:66]=2)[CH:60]2[N:73]([C:76](=[O:83])[CH:77]([NH:82][C:11](=[O:13])[CH:9]([N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:14])[CH3:10])[C:78]([CH3:79])([CH3:81])[CH3:80])[CH2:74][CH2:75][CH:59]12)=[O:57])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67517814HCID 67517814, compound

Product 1

HCID 67606716HCID 67606716, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of Boc-N(Me)Ala-OH (181 mg, 0.89 mmol) in NMP (6 mL) was cooled to 0° C. and treated with HATU (345 mg, 0.91 mmol) and DIPEA (0.20 mL, 1.2 mmol). After 10 min, amine 82 (400 mg, 0.80 mmol) in NMP (5 mL) was added and the reaction mixture was allowed to warm to ambient temperature. After 16 h, the solution was diluted with EtOAc, washed successively with 1M HCl, saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered and concentrated to give 83 (546 mg) as an off-white foam that was used without further purification. 1H NMR (CDCl3, 300 MHz): δ7.37-7.29 (m, 5H), 7.01 (app q, J=9.3 Hz, 1H), 6.66 (m, 1H), 6.53 (m, 1H), 5.19-5.09 (m, 2H), 4.69 (m, 1H), 4.62 (d, J=9.0 Hz, 1H), 4.49-4.44 (m, 2H), 4.05-3.97 (m, 1H), 3.84-3.77 (m, 1H), 3.48-3.36 (m, 1H), 2.79 (s, 3H), 1.50 (s, 9H), 1.32 (d, J=6.9 Hz, 3H), 0.98 (s, 9H) ppm. Mass spectrum, m/z [687.9] (M+H)+.

Workup

  1. waitAfter 16 h
  2. washwashed successively with 1M HCl, saturated aqueous NaHCO3, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4cde16bb47ff456f88cb64c5590c0eee
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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