4-Methylmorpholine → HCID 67408599, compound

HRID 1949645Notes

Reaction equation

HRID 1949645 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.CN1CCOCC1.[NH2:46][CH:47]([CH2:72][CH3:73])[C:48]([N:50]1[CH2:54][CH2:53][CH:52]2[N:55]([S:68]([CH3:71])(=[O:70])=[O:69])[CH2:56][CH:57]([C:58]3[C:66]4[C:61](=[CH:62][C:63]([F:67])=[CH:64][CH:65]=4)[NH:60][CH:59]=3)[CH:51]12)=[O:49]>CN1C(=O)CCC1.C(OCC)C.CCOC(C)=O>[C:4]([O:3][C:1](=[O:2])[N:8]([CH:9]([C:11](=[O:13])[NH:46][CH:47]([C:48]([N:50]1[CH2:54][CH2:53][CH:52]2[N:55]([S:68]([CH3:71])(=[O:69])=[O:70])[CH2:56][CH:57]([C:58]3[C:66]4[C:61](=[CH:62][C:63]([F:67])=[CH:64][CH:65]=4)[NH:60][CH:59]=3)[CH:51]12)=[O:49])[CH2:72][CH3:73])[CH3:10])[CH3:14])([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 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 67407504HCID 67407504, compound

Product 1

HCID 67408599HCID 67408599, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution containing Boc-N(Me)Ala-OH (85 mg, 0.41 mmol) in anhydrous NMP (2 mL) was cooled to 0° C. HATU (156 mg, 0.41 mmol) and NMM (51 mg, 0.5 mmol) were added followed by the addition of crude 65 (150 mg, 0.37 mmol) in anhydrous NMP (4 mL). The reaction mixture was slowly warmed to ambient temperature. After 16 h, the reaction mixture was diluted with diethyl ether and EtOAc (10:1) and washed successively with aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 160 mg of crude 66 which was used without further purification. Mass spectrum, m/z [594.2] (M+H)+.

Workup

  1. temperatureThe reaction mixture was slowly warmed to ambient temperature
  2. washwashed successively with aqueous NaHCO3 and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford 160 mg of crude 66 which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-839d1b44b5884c9c955b3a8128f748fa
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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