4-Methylmorpholine → HCID 67148581, compound

HRID 1054010Notes

Reaction equation

HRID 1054010 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][CH2:12][NH2:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C(ON1N=N[C:27]2[CH:28]=[CH:29][CH:30]=N[C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1[CH2:47][CH2:46][O:45][CH2:44]C1.[CH2:48]([O:50][C:51](=[O:69])[CH2:52][CH2:53][C:54]1[O:55][C:56]2[CH:68]=[CH:67][CH:66]=[CH:65][C:57]=2[C:58]=1[CH2:59][CH:60]1[CH2:64][CH2:63][CH2:62][NH:61]1)[CH3:49].CN1C(=[O:76])CCC1>C(OCC)C>[CH2:48]([O:50][C:51](=[O:69])[CH2:52][CH2:53][C:54]1[O:55][C:56]2[CH:68]=[CH:67][CH:66]=[CH:65][C:57]=2[C:58]=1[CH2:59][CH:60]1[CH2:64][CH2:63][CH2:62][N:61]1[C:14](=[O:16])[CH:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:10][CH2:11][CH2:12][NH:13][C:44]([O:45][CH2:46][C:47]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:76])[CH3:49]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 13387N-methyl-2-pyrrolidone2×HCID 7018784(2S)-5-amino-2-{[(tert-butoxy)carbonyl]amino}pentanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67148063HCID 67148063, compound

Product 1

HCID 67148581HCID 67148581, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution containing Boc-L-ornithine (2.3 g, 6.3 mmol) in NMP (5 mL) was treated with HATU (2.4 g, 6.3 mmol) followed by NMM (1.5 mL, 13.7 mmol) at ambient temperature. After 10 min, amine 48 (1.6 g, 5.3 mmol) in NMP (10 mL) was added in a dropwise fashion. After 16 h, the reaction mixture was diluted with diethyl ether and washed successively with NaHCO3, 1 M HCl, water, and brine. The organic extract was dried over anhydrous Na2SO4, filtered and concentrated to afford 3.0 g (87%) of 53 as an orange-colored oil which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ7.78-7.75 (m, 1H), 7.40-7.20 (m, 8H), 5.48 (d, J=8.4 Hz, 1H), 5.10 (s, 2H), 4.48-4.42 (m, 1H), 4.17-4.09 (m, 2H), 3.64-3.56 (m, 1H), 3.27-3.19 (m, 1H), 3.12 (app t, J=7.8 Hz, 1H), 2.81-2.74 (m, 2H), 2.52-2.35 (m, 1H), 2.09-1.95 (m, 2H), 1.83-1.63 (m, 4H), 1.45 (s, 9H), 1.29-1.19 (m, 6H) ppm.

Workup

  1. waitAfter 16 h
  2. washwashed successively with NaHCO3, 1 M HCl, water, and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7e3cb73bfd8e496bb310b1d09a96938e
Source dataset
uspto-grants-2016_07
Patent number
US09394249B2

Reaction notes

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