Water → tert-butyl ((1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

HRID 1051029ノート

反応式

HRID 1051029 の反応式
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])[N:14]([S:16]([C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=2)[O:22][CH2:23][C:24](O)=[O:25])(=[O:18])=[O:17])[CH:15]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:50]2[N:51]=[CH:52]C=CC=2N=N1.O>O1CCCC1.C(OCC)(=O)C>[CH3:50][N:51]([CH3:52])[C:24](=[O:25])[CH2:23][O:22][C:21]1[CH:20]=[C:19]([S:16]([N:14]2[C:13]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])=[CH:12][C:11]([CH2:10][N:8]([CH3:9])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:15]2)(=[O:18])=[O:17])[CH:29]=[CH:28][CH:27]=1

参加物

7

反応物 4

HCID 962WaterHCID 6329MethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 901689202-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid

生成物 1

HCID 90168924tert-butyl ((1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-(3-((4-(((tert-Butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid 9b (170 mg, 0.33 mmol) was added to a solution of methylamine in tetrahydrofuran (2 N, 5 mL), followed by addition of 2-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (104 mg, 0.91 mmol) and then the reaction solution was stirred for 3 h. 20 mL of water and 20 mL of ethyl acetate were added, and the reaction solution was layered, the water phase was extracted with ethyl acetate (20 mL×1). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by thin layer chromatography with elution system C to obtain the title product tert-butyl ((1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 9c (50 mg, a white solid) in 28% yield.

後処理

  1. extractionthe water phase was extracted with ethyl acetate (20 mL×1)
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by thin layer chromatography with elution system C

出典と根拠

ORDレコード
ord-e2e15dc5e63d48f5a0b9f99447cc4d33
出典データセット
uspto-grants-2016_07
特許番号
US09388133B2

反応ノート

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