Diisopropylethylamine → (2S,5R)-6-(allyloxy)-N-((4,5-bis(4-methoxybenzyloxy)pyridin-2-yl)methyl)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627116Notes

Reaction equation

HRID 627116 reaction equation
[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([CH3:17])=[CH:8][C@@H:9]2[C:14]([OH:16])=O)[CH:2]=[CH2:3].[CH3:18][O:19][C:20]1[CH:45]=[CH:44][C:23]([CH2:24][O:25][C:26]2[C:31]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)=[CH:30][N:29]=[C:28]([CH2:42][NH2:43])[CH:27]=2)=[CH:22][CH:21]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([CH3:17])=[CH:8][C@H:9]2[C:14]([NH:43][CH2:42][C:28]1[CH:27]=[C:26]([O:25][CH2:24][C:23]2[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:45][CH:44]=2)[C:31]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=2)=[CH:30][N:29]=1)=[O:16])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89851364(4,5-Bis(4-methoxybenzyloxy)pyridin-2-yl)methanamine2×HCID 89852904(2R,5R)-6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxylic acid2×

Product 1

HCID 89852060(2S,5R)-6-(allyloxy)-N-((4,5-bis(4-methoxybenzyloxy)pyridin-2-yl)methyl)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideYield 36.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxylic acid (Intermediate 32, 0.469 g, 1.97 mmol) in DMF (10 mL) at room temperature was added (4,5-bis(4-methoxybenzyloxy)pyridin-2-yl)methanamine (Intermediate 65, 0.824 g, 2.17 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.497 g, 3.94 mmol) and N,N-diisopropylethylamine (1.372 mL, 7.87 mmol). After 30 minutes the reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate, brine, and 1/1 brine/water twice. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-50% ethyl acetate/hexanes) afforded the title compound as a light pink foam (0.427 g, 36%).

Workup

  1. washwashed with saturated sodium bicarbonate, brine, and 1/1 brine/water twice
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ce4c6dec6dd44b5489ef651fd8447929
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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