Triethylamine → [3-(3-Chloromethyl-[1,2,4]oxadiazol-5-yl)-phenyl]-methanol

HRID 732039ノート

反応式

HRID 732039 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[Cl:12][CH2:13][C:14]([NH:16]O)=[NH:15].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[Cl:12][CH2:13][C:14]1[N:16]=[C:6]([C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:11]=[CH:10][CH:9]=2)[O:8][N:15]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 185629Benzoic acid, 3-(hydroxymethyl)-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178511097HCID 178511097、化合物

生成物 1

HCID 67070834[3-(3-Chloromethyl-[1,2,4]oxadiazol-5-yl)-phenyl]-methanol収率 25%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Hydroxymethylbenzoic acid, described in Reed, G. A.; Dimmel, D. R.; Malcolm, E. W. J. Org. Chem. 1993, 58 (23), 6372-6376, (175 mg, 1.15 mmol), 2-chloro-N-hydroxy-acetamidine (125 mg, 1.15 mmol) and HBTU was dissolved in anhydrous DMF (4 ml). Triethylamine (0.48 ml, 3.5 mmol) was added and the reaction was stirred at ambient temperature over night. The crude product was partitioned between dichloromethane and NaHCO3 (aq), the organic phase was dried (MgSO4) and the dichloromethane was removed in vacuo. The resulting DMF-solution was heated at 120° C. over night. The reaction mixture was concentrated in vacuo and the title compound (64 mg, 25%) was isolated by flash chromatography using 25-50% ethyl acetate in heptane. 1H NMR (CDCl3), δ (ppm): 8.15 (s, 1H), 8.06 (d, 1H), 7.62 (d, 1H), 7.53 (t, 1H); 4.80 (d, 2H), 4.66 (s, 1H); 1.99 (br. t, 1H).

後処理

  1. customThe crude product was partitioned between dichloromethane and NaHCO3 (aq)
  2. dry with materialthe organic phase was dried (MgSO4)
  3. customthe dichloromethane was removed in vacuo
  4. temperatureThe resulting DMF-solution was heated at 120° C. over night
  5. concentrationThe reaction mixture was concentrated in vacuo

出典と根拠

ORDレコード
ord-033d605065f34e83b2dcea8a47dcb8d3
出典データセット
uspto-grants-2009_09
特許番号
US07585881B2

反応ノート

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