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

HRID 1677022

반응식

HRID 1677022 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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 44) (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.

후처리

  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

출처 및 근거

ORD 기록
ord-391b835b45b84529a8172266acc19ce1
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008291B2

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