2-Naphthoic acid → N-(2-(methoxy(methyl)amino)-2-oxoethyl)-2-naphthamide

HRID 524323

Reaction equation

HRID 524323 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.[NH2:14][CH2:15][C:16]([N:18]([O:20][CH3:21])[CH3:19])=[O:17].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:21][O:20][N:18]([CH3:19])[C:16](=[O:17])[CH2:15][NH:14][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:13]

Participants

7

Reactant 5

HCID 71232-Naphthoic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 103292782-amino-N-methoxy-N-methylacetamide

Product 1

HCID 45866900N-(2-(methoxy(methyl)amino)-2-oxoethyl)-2-naphthamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-naphthoic acid (5.8 g, 33.7 mmol), 2-amino-N-methoxy-N-methylacetamide (Gly Weinreb amide; prepared from Boc-Gly Weinreb amide 15 as in Example 43) (3.8 g, 32.1 mmol) and DIPEA (12.0 mL, 68.9 mmol) in DCM (70 mL) was added BOP (14.9 g, 33.7 mmol) in one portion at room temperature. The resulting mixture was stirred for 1 hr then saturated NaHCO3 aqueous solution was added. The organic layer was washed with brine (5×60 mL) and 1 N HCl (2×30 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give the crude product, which was used in the next reaction without further purification.

Workup

  1. washThe organic layer was washed with brine (5×60 mL) and 1 N HCl (2×30 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2fae8f2338064ab1a1a6fe55ea671e8c
Source dataset
uspto-grants-2016_05
Patent number
US09340517B2

Linked notes

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