Methylamine → HCID 53240651, compound

HRID 422163Notes

Reaction equation

HRID 422163 reaction equation
[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:25])[C@H:15]([CH2:16][S:17]2(=[O:21])=[O:20])[C@:14]2([CH3:22])[C@H:9]([C:10]([CH3:24])([CH3:23])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[C:4]([C:26]([OH:28])=O)[CH:3]=1.[CH3:29][N:30](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.CN>CN(C=O)C.C1COCC1>[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:25])[C@H:15]([CH2:16][S:17]2(=[O:21])=[O:20])[C@:14]2([CH3:22])[C@H:9]([C:10]([CH3:24])([CH3:23])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[C:4]([C:26]([NH:30][CH3:29])=[O:28])[CH:3]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53240650HCID 53240650, compound

Product 1

HCID 53240651HCID 53240651, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carboxylic acid (65) (0.49 g, 1.2 mmol), HATU (0.70 g, 1.8 mmol), N-methyl morpholine (0.40 mL, 3.6 mmol), methylamine (2 M in THF, 3.0 mL, 6.0 mmol), THF (10 mL) and DMF (2.0 mL) were placed in a sealed tube. The mixture was stirred at room temperature for 18 h. The THF was evaporated and the residue was quenched with water. The resulting solid was collected by filtration. The crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 1:1) to yield (1R,10R,11S,16S)-5-hydroxy-N,1,11,15,15-pentamethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carboxamide (66) (0.25 g, 44%) as a white solid. 1H NMR (CDCl3): δ 7.62 (s, 1H), 7.09 (s, 1H), 6.70 (s, 1H), 6.36 (m, 1H), 3.39 (m, 2H), 2.97 (d, 3H), 2.54 (m, 1H), 2.13 (m, 1H), 1.75-0.96 (m, 13H), 0.94 (s, 3H), 0.88 (s, 3H), 0.82 (s, 3H). MS m/z 420 (C23H33NO4S+H+).

Workup

  1. customwere placed in a sealed tube
  2. customThe THF was evaporated
  3. customthe residue was quenched with water
  4. filtrationThe resulting solid was collected by filtration
  5. customThe crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-7796ab0d49e8476d9e180269611da21a
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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