Triphenylphosphine → 7-[2-(N-tert-butoxycarbonyl-N-methylamino)ethoxyl]-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester

HRID 272803

반응식

HRID 272803 반응식
[C:1]([O:5][C:6]([N:8]([CH2:10][CH2:11][OH:12])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:13][O:14][C:15]([C:17]1[C:18](=[O:28])[O:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[C:22](O)[CH:21]=2)=[O:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:13][O:14][C:15]([C:17]1[C:18](=[O:28])[O:19][C:20]2[CH:21]=[C:22]([O:12][CH2:11][CH2:10][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:9])[CH:23]=[CH:24][C:25]=2[CH:26]=1)=[O:16]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 5416969Methyl 7-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate

생성물 1

HCID 103849407-[2-(N-tert-butoxycarbonyl-N-methylamino)ethoxyl]-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester수율 73.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-(N-tert-butoxycarbonyl-N-methylamino)ethanol (0.5 g, 3 mmol) and 7-hydroxyl-3-coumarin carboxylic acid methyl ester (0.6 g, 3 mmol) are dissolved in 60 mL of anhydrous tetrahydrofuran. Triphenylphosphine (1.2 g, 4.5 mmol) is added, and diethyl azodicarboxylate (720 μL, 0.45 mmol) is added dropwise and slowly at 0° C. The resulting solution is stirred at room temperature for 24 hours. After the solvent was removed under reduced pressure at 30° C., the residue is mixed with methanol at room temperature. A solid is produced by filtrating under reduced pressure and 0.83 g of the captioned compound is obtained, yield: 72.6%. m.p. 128-129° C. 1H NMR(DMCO-d6): δ=1.40(s, 9H), 2.96(s, 3H), 3.65(s, 2H), 3.81(s, 3H), 4.32(s, 2H), 6.94(d, J=2.2 Hz, 1H), 7.00(dd, J=2.2 Hz, 8.4 Hz, 1H), 7.80(d, J=8.8 Hz, 1H), 8.60 (s,1H); EI-MS(m/z): 377(1, M+), 102(100).

후처리

  1. customAfter the solvent was removed under reduced pressure at 30° C.
  2. additionthe residue is mixed with methanol at room temperature
  3. customA solid is produced
  4. filtrationby filtrating under reduced pressure

출처 및 근거

ORD 기록
ord-63a3ed5db00e48769b6b29c990640ae3
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456205B2

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