Triphenylphosphine → tert-butyl N-(3-methylsulfonylpropyl)-N-[[5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octan-8-yl]sulfonyl]carbamate

HRID 589985ノート

反応式

HRID 589985 の反応式
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:17][CH2:16][N:15]([S:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:20])=[O:19])[C:12]3([CH2:14][CH2:13]3)[CH2:11]2)=[N:3][CH:2]=1.[CH3:29][S:30]([CH2:33][CH2:34][CH2:35]O)(=[O:32])=[O:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(/N=N\C(=O)OC(C)C)=O)(C)C>C1COCC1.O>[CH3:29][S:30]([CH2:33][CH2:34][CH2:35][N:21]([S:18]([N:15]1[C:12]2([CH2:14][CH2:13]2)[CH2:11][N:10]([C:4]2[C:5]3[CH:9]=[CH:8][NH:7][C:6]=3[N:1]=[CH:2][N:3]=2)[CH2:17][CH2:16]1)(=[O:19])=[O:20])[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])(=[O:32])=[O:31]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 2004243-(Methylsulfonyl)-1-propanolHCID 567765201-Diazene-1,2-dicarboxylic acid, 1,2-bis(1-methylethyl) ester, (1Z)-HCID 68296038tert-butyl N-[[5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octan-8-yl]sulfonyl]carbamate2 回

生成物 1

HCID 57410100tert-butyl N-(3-methylsulfonylpropyl)-N-[[5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octan-8-yl]sulfonyl]carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Tert-butyl N—[[5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octan-8-yl]sulfonyl]carbamate (Intermediate 53)(0.12 mmol) was dissolved in dry THF (1 mL) and added 3-methylsulfonylpropan-1-ol (0.13 mmol) and triphenylphosphine (0.15 mmol). The reaction mixture was cooled to 0° C. and slowly added isopropyl (NZ)—N-isopropoxycarbonyliminocarbamate (0.15 mmol). The reaction mixture was allowed to warm up freely to rt and stirred at rt for 16 h. The crude mixture was treated with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic phases were washed with H2O (2×50 mL), brine (2×50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica using EtOAc in heptane as eluent.

後処理

  1. temperatureto warm up freely to rt
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic phases were washed with H2O (2×50 mL), brine (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-cee68025b62d4511a4d384de2d3362bc
出典データセット
uspto-grants-2016_01
特許番号
US09233964B2

反応ノート

読み込み中…