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Methylamine → HCID 86654195, 화합물

HRID 422167
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HRID 422167 반응식
[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:24])[C@H:15]([CH2:16][S:17]2=[O:20])[C@:14]2([CH3:21])[C@H:9]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[CH:4][C:3]=1[C:25]([OH:27])=O.[CH3:28][N:29](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN>C1COCC1.CN(C=O)C.CCOC(C)=O>[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:24])[C@H:15]([CH2:16][S:17]2=[O:20])[C@:14]2([CH3:21])[C@H:9]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[CH:4][C:3]=1[C:25]([NH:29][CH3:28])=[O:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58294800(1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8-oxo-8lambda4-thiatetracyclo-[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4-carboxylic acid

생성물 1

HCID 86654195
HCID 86654195, 화합물
수율 16%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of (1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8-oxo-8λ4-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4-carboxylic acid (71) (0.40 g, 1.1 mmol), HATU (0.49 g, 1.3 mmol), Hunig's base (0.24 mL, 1.4 mmol), methylamine (2 M in diethyl ether, 2.7 mL, 5.4 mmol) in anhydrous THF (10 mL) and DMF (2 mL) was placed in a sealed vessel. The reaction was stirred at room temperature for 18 h. The reaction was diluted with EtOAc and washed with water and brine. The organic layer was separated and concentrated to dryness. The crude product was purified by flash chromatography on silica gel (CH2Cl2/EtOAc, 7:3) to yield (1R,10R,11S,16S)-5-hydroxy-N,1,11,15,15-pentamethyl-8-oxo-8λ4-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4-carboxamide (72) (0.07 g, 16% yield) as a white solid.

후처리

  1. customwas placed in a sealed vessel
  2. washwashed with water and brine
  3. customThe organic layer was separated
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2/EtOAc, 7:3)

출처 및 근거

ORD 기록
ord-1b26392101a74af7b3ad53a94a2e1e6d
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08101605B2

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