Trifluoroacetic acid → 3-(4-(1-(3-Hydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

HRID 1582372

反応式

HRID 1582372 の反応式
[OH:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]([C:12]2[C:17]([F:18])=[CH:16][C:15]([N:19]3[CH2:23][C@H:22]([CH2:24][N:25]([C:33]4[CH:37]=[CH:36][O:35][N:34]=4)C(OC(C)(C)C)=O)[O:21][C:20]3=[O:38])=[CH:14][C:13]=2[F:39])=[CH:8][CH2:7]1)=[O:5].FC(F)(F)C(O)=O>ClCCl.O>[OH:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]([C:12]2[C:13]([F:39])=[CH:14][C:15]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:33]4[CH:37]=[CH:36][O:35][N:34]=4)[O:21][C:20]3=[O:38])=[CH:16][C:17]=2[F:18])=[CH:8][CH2:7]1)=[O:5]

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 571925683-(4-(1-(3-Hydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

生成物 1

HCID 698904443-(4-(1-(3-Hydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one収率 70.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

3-(4-(1-(3-Hydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (176 mg, 0.32 mM), was dissolved in dichloromethane (1 ml) and treated with trifluoroacetic acid (1 ml) at ambient temperature. After stirring for 10 minutes, the mixture was diluted with water (15 ml) and dichloromethane (15 ml), the organic layer separated, washed with water (2×15 ml), and dried (magnesium sulfate). Solvent was removed, and the residue triturated with diethyl ether to give the desired product (102 mg). NMR (DMSO-d6) δ: 2.20 (m, 1H); 2.28 (m, 1H); 2.48 (m overlapped by DMSO, 2H); 3.42 (br m overlapped by H2O, ˜4H); 3.55 (br m, ˜3H); 3.83 (t, 1H); 4.01 (m, 1H); 4.06 (m, 2H); 4.81 (m, 1H); 5.78 (s, 1H); 5.92 (s, 1H); 6.47 (br s, 1H); 7.26 (d, 2H); 8.31 (s, 1H). MS (ESP): 449 (MH+) for C21H22F2N4O5

後処理

  1. customthe organic layer separated
  2. washwashed with water (2×15 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customSolvent was removed
  5. customthe residue triturated with diethyl ether

出典と根拠

ORDレコード
ord-40086570b4784eb787b5caaa667659a9
出典データセット
uspto-grants-2004_05
特許番号
US06734200B1

関連ノート

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