Trifluoroacetic acid → N-((3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl)-6-chloronaphthalene-2-sulfonamide

HRID 7300

反応式

HRID 7300 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C@@H:21]([CH3:38])[C:22]([N:24]3[CH2:29][CH2:28][CH2:27][CH:26]([NH:30]C(=O)OC(C)(C)C)[CH2:25]3)=[O:23])[C:17]1=[O:39])(=[O:14])=[O:13])[CH:6]=[CH:5]2.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:30][CH:26]1[CH2:27][CH2:28][CH2:29][N:24]([C:22](=[O:23])[C@@H:21]([N:18]2[CH2:19][CH2:20][C@H:16]([NH:15][S:12]([C:7]3[CH:6]=[CH:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=4)[CH:8]=3)(=[O:14])=[O:13])[C:17]2=[O:39])[CH3:38])[CH2:25]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 69823661tert-Butyl 1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate

生成物 1

HCID 69329851N-((3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl)-6-chloronaphthalene-2-sulfonamide収率 76.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-Butyl 1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate (0.6 g) was dissolved in DCM (11 ml) and trifluoroacetic acid (11 ml) was added. The mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The residue was dissolved in water (5 ml) and ammonia solution (0.88%; 1 ml) added. The resultant aqueous mixture was extracted with DCM. The combined organic extracts were dried (over magnesium sulphate), filtered and concentrated under reduced pressure to give the title compound (0.38 g) as a white foam.

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (5 ml)
  3. additionammonia solution (0.88%; 1 ml) added
  4. extractionThe resultant aqueous mixture was extracted with DCM
  5. dry with materialThe combined organic extracts were dried (over magnesium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-eb3527bffa1344d285bd826e249706ce
出典データセット
uspto-grants-2006_08
特許番号
US07084139B2

関連ノート

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