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Triethylamine → ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]acrylate

HRID 369360
ノート
印刷プレビュー

反応式

HRID 369360 の反応式
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C@H:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]2)=[CH:9][CH:8]=1)(=O)=O.[C:27]([O:31][CH2:32][CH3:33])(=[O:30])[CH:28]=[CH2:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:21]([O:20][C:18]([NH:17][C@H:13]1[CH2:12][CH2:11][C:10]2[C:15](=[CH:16][C:7]([CH:29]=[CH:28][C:27]([O:31][CH2:32][CH3:33])=[O:30])=[CH:8][CH:9]=2)[CH2:14]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471Triethylamine2 回HCID 8821Ethyl Acrylate2 回HCID 11776TriphenylphosphineHCID 18651771(S)-2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl trifluoromethanesulfonate

生成物 1

HCID 57134535ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]acrylate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 962Water溶媒

実験手順

(S)-2-(tert-Butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl trifluoromethanesulfonate (500 mg), ethyl acrylate (179 μl), triphenylphosphine (22 mg), palladium acetate (9.3 mg) and triethylamine (250 μl) were allowed to react for 6 hours at 90° C. and for 5 hours at 100° C. with stirring. Ethyl acrylate (97 μl), triethylamine (125 μl) and bis(triphenylphosphine)palladium(II) dichloride (27 mg) were added to the reaction mixture, followed by reaction for 11 hours at 100° C. with stirring. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with 1 N hydrochloric acid and 0.5 M aqueous phosphate buffer solution (pH 7) sequentially, and dried over anhydrous magnesium sulfate, then the solvent was removed in vacuo. Purification by medium pressure liquid column chromatography on silica gel (eluent: dichloromethane/ethyl acetate=20/1) and sequential recrystallization from diisopropyl ether of the residue gave ethyl (S)-3-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]acrylate (252 mg) having a melting point of 99-100° C.

後処理

  1. customto react for 6 hours at 90° C. and for 5 hours at 100° C.
  2. customfollowed by reaction for 11 hours at 100° C.
  3. stirringwith stirring
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with 1 N hydrochloric acid and 0.5 M aqueous phosphate buffer solution (pH 7) sequentially
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customPurification by medium pressure liquid column chromatography
  9. customon silica gel (eluent: dichloromethane/ethyl acetate=20/1) and sequential recrystallization from diisopropyl ether of the residue

出典と根拠

ORDレコード
ord-3bb1ef8a37f44622b65b2a1c54dac830
出典データセット
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06136852

反応ノート

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