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 589985노트

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HRID 589985 반응식
[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]

참가 물질

7

반응물 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]carbamate2회

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cee68025b62d4511a4d384de2d3362bc
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233964B2

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