Triphenylphosphine → 5-((2S)-3-Amino-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl ester

HRID 1794793ノート

反応式

HRID 1794793 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C@@H:17]([OH:22])[CH2:18][N:19]=[N+]=[N-])[CH:13]=2)[NH:8][C:7]=1[CH3:23])=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C@@H:17]([OH:22])[CH2:18][NH2:19])[CH:13]=2)[NH:8][C:7]=1[CH3:23])=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 865845645-((2S)-3-Azido-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl ester

生成物 1

HCID 696549695-((2S)-3-Amino-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl ester収率 101.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 0.56 g (1.76 mmol) of 5-((2S)-3-azido-2-hydroxy-propoxy)-2-methyl-1H-indole-3-carboxylic acid ethyl ester (which was obtained in Example 140) and 1.2 g of triphenylphosphine polymer resin (3 mmol/g) was stirred in 15 mL toluene for 1.5 hours under nitrogen. The resin was collected by filtration and washed twice with 25 mL of toluene. The resin was then stirred in 60 mL of 9:1 THF/methanol for four hours. The resin was removed by vacuum filtration and washed with 9:1 THF/methanol. The filtrate was concentrated in vacuo. Then the solid was dried under vacuum to give 0.52 g of the title compound as a beige solid; mp 66–68° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.32–1.37 (m, 3H), 1.80 (brs, 1H), 2.61 (s, 3H), 2.69–2.75 (m, 2H), 3.69–3.76 (m, 1H), 3.82–3.95 (m, 2H), 4.23 (q, J=6.93 Hz, 2H), 4.90 (brs, 1H), 6.76 (dd, J=2.52 Hz, 8.73 Hz, 1H), 7.23 (d, J=8.7 Hz, 1H), 7.43 (d, J=2.4 Hz, 1H), 8.85 (brs, 1H), 11.65 (s, 1H); MS (ES) m/z: 293.0 (MH+); HRMS Calcd. for C15H21N2O4(MH+): 293.1501. Found: 293.1498.

後処理

  1. filtrationThe resin was collected by filtration
  2. washwashed twice with 25 mL of toluene
  3. customThe resin was removed by vacuum filtration
  4. washwashed with 9:1 THF/methanol
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThen the solid was dried under vacuum

出典と根拠

ORDレコード
ord-ac435a2a84b9499fa4daade486400aff
出典データセット
uspto-grants-2006_04
特許番号
US07022716B2

反応ノート

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