Methylamine → (1R,10R,11S,16S)-3-methoxy-N,1,11,15,15-pentamethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxamide

HRID 422174Notes

Reaction equation

HRID 422174 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([C:21](O)=[O:22])[CH:18]=[C:17]2[C:4]=1[C@@:5]1([CH3:29])[C@H:14]([CH2:15][S:16]2(=[O:25])=[O:24])[C@:13]2([CH3:26])[C@H:8]([C:9]([CH3:28])([CH3:27])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1.[CH3:30][N:31](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.CN>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:20]=[C:19]([C:21]([NH:31][CH3:30])=[O:22])[CH:18]=[C:17]2[C:4]=1[C@@:5]1([CH3:29])[C@H:14]([CH2:15][S:16]2(=[O:25])=[O:24])[C@:13]2([CH3:26])[C@H:8]([C:9]([CH3:28])([CH3:27])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]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 53240648(1R,10R,11S,16S)-3-methoxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid

Product 1

HCID 53240649(1R,10R,11S,16S)-3-methoxy-N,1,11,15,15-pentamethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxamideYield 41.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1R,10R,11S,16S)-3-methoxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid (80) (0.26 g, 0.61 mmol), HATU, (0.36 g, 0.93 mmol), NMM (0.20 mL, 1.9 mmol) and methylamine (2 M in THF, 1.5 mL, 3.0 mmol) in THF (10 mL) and DMF (2.0 mL) was stirred at room temperature for 18 h in a sealed tube. The reaction mixture was concentrated under reduced pressure and the residue was quenched with water. The resulting solid was collected by filtration to give (1R,10R,11S,16S)-3-methoxy-N,1,11,15,15-pentamethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxamide (81) (0.11 g, 41%) as a white solid. 1H NMR (CDCl3): δ 7.67 (d, 1H), 7.61 (d, 1H), 6.27 (s, 1H), 3.91 (s, 3H), 3.40-3.17 (m, 3H), 3.01 (d, 3H), 2.30 (d, 1H), 1.78-1.28 (m, 10H), 1.23-1.00 (m, 3H), 0.97 (s, 3H), 0.87 (s, 3H), 0.84 (s, 3H). MS m/z 434 (C24H35NO4S+H+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was quenched with water
  3. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-e25aed608b3e4072937a1e38c9561d80
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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