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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0

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Nitric Acid → (4aS,5S,7aS)-7a-(2,3-difluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

HRID 707709

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HRID 707709 반응식

[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:17][O:16][C@H:15]([CH2:18][F:19])[C@H:14]1[CH2:13][S:12][C:11]([NH2:20])=[N:10]2.S(=O)(=O)(O)O.[N+:26]([O-])([OH:28])=[O:27].[OH-].[Na+]>FC(F)(F)C(O)=O>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:26]([O-:28])=[O:27])=[CH:4][C:3]=1[C@:9]12[CH2:17][O:16][C@H:15]([CH2:18][F:19])[C@H:14]1[CH2:13][S:12][C:11]([NH2:20])=[N:10]2

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참가 물질

6

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HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 14798Sodium Hydroxide

HCID 60168237(4aS,5S,7aS)-7a-(2,3-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

생성물 1

HCID 60168239(4aS,5S,7aS)-7a-(2,3-difluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도: 0 °C

실험 절차

(4aS,5S,7aS)-7a-(2,3-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (9.10 g, 0.03 mol, 1.0 equiv.) was dissolved in trifluoroacetic acid (36.4 mL), and the solution was cooled to 0° C. Sulfuric acid (conc., 12.0 mL) was added, followed by fuming nitric acid (6.9 mL) dropwise while maintaining the temperature below 5° C. After stirring at 0-5° C. for 4 h, the reaction mixture was slowly charged into a vigorously stirred solution of aq.NaOH (43.3 g in 273 mL water) while maintaining a temperature below 20° C. The mixture was extracted with CH2Cl2 (1×94 ml, and 2×64 mL), and the combined organic phases were washed with sat. aq. NaCl (46 mL). Celite (15.0 g) was added to the organics, and the mixture was filtered rinsing with CH2Cl2 (40 mL). The solvents were evaporated to afford the title compound (8.3 g) which was used in the subsequent step without purification. 1H NMR (500 MHz, DMSO) δ ppm 8.41-8.30 (m, 1H), 8.22-8.13 (m, 1H), 6.36 (s, 2H), 4.70-4.46 (m, 2H), 4.43-4.31 (m, 1H), 4.35 (d, J=8.7 Hz, 1H), 3.69 (dd, J=8.5, 1.6 Hz, 1H), 3.04-2.91 (m, 2H), 2.86-2.76 (m, 1H); 13C NMR (125 MHz, DMSO) δ ppm 152.36 (dd, JCF=246.8, 12.3 Hz), 151.13, 150.32 (dd, JCF=238.2, 12.2 Hz), 143.25 (dd, JCF=7.9, 2.5 Hz), 134.70 (d, JCF=9.5 Hz), 121.28, 113.02 (d, JCF=22.3 Hz), 83.74 (d, JCF=170.1 Hz), 79.44 (d, JCF=18.3 Hz), 78.02 (d, J=3.9 Hz), 36.96, 23.28.

후처리

temperaturewhile maintaining the temperature below 5° C
additionthe reaction mixture was slowly charged into a vigorously stirred solution of aq
extractionThe mixture was extracted with CH2Cl2 (1×94 ml, and 2×64 mL)
washthe combined organic phases were washed with sat. aq. NaCl (46 mL)
additionCelite (15.0 g) was added to the organics, and the mixture
filtrationwas filtered
washrinsing with CH2Cl2 (40 mL)
customThe solvents were evaporated

출처 및 근거

ORD 기록: ord-41187163ffb64d8cbadbebc7b7a92164
출처 데이터셋: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09175013B2

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