Triphenylphosphine → t-Butyl N-[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methylbutyl]-N-methylsulfonylcarbamate

HRID 748787ノート

反応式

HRID 748787 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[CH:12]([CH3:16])[CH2:13][CH2:14]O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:25][S:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:28])=[O:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O-])=O)=NC([O-])=O>O1CCCC1.C(OCC)(=O)C.CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[CH:12]([CH3:16])[CH2:13][CH2:14][N:29]([S:26]([CH3:25])(=[O:28])=[O:27])[C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])(=[O:10])=[O:9])=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 10081367tert-Butyl methylsulfonylcarbamateHCID 230288584-(4-Chlorophenylsulfonyl)-4-(2,5-difluorophenyl)-3-methyl-1-butanolHCID 51573101N-carboxylatoiminocarbamate

生成物 1

HCID 59750918t-Butyl N-[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methylbutyl]-N-methylsulfonylcarbamate収率 95%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methyl-1-butanol (97.2 mg, 0.259 mmol) obtained in Example 239, t-butyl N-methylsulfonylcarbamate (101 mg, 0.518 mmol) and triphenylphosphine (138 mg, 0.518 mmol) were dissolved in tetrahydrofuran (3 ml), followed by the addition of diisoopropyl azodicarboxylate (102 μl, 0.518 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of ammonium chloride, water and brine, dried over magnesium sulfate and then concenetrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=3:2 eluate was concentrated, whereby the title compound (136 mg, 0.246 mmol, 95%) was obtained as a colorless amorphous substance.

後処理

  1. washwashed with a saturated aqueous solution of ammonium chloride, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe residue thus obtained
  4. concentrationethyl acetate=3:2 eluate was concentrated

出典と根拠

ORDレコード
ord-9a178c1732f54e668839a27f67d06acf
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

反応ノート

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