Hydrochloric Acid → 2-(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-1-oxo-ethyl-valinyl-valine methyl ester

HRID 1755818ノート

反応式

HRID 1755818 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22](O)=[O:23])[C:17](=[O:25])[CH:16]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C2N=NNC=2C=CC=1.Cl.[NH2:44][C@H:45]([C:49]([NH:51][C@H:52]([C:56]([O:58][CH3:59])=[O:57])[CH:53]([CH3:55])[CH3:54])=[O:50])[CH:46]([CH3:48])[CH3:47].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.C(N(CC)CC)C>[CH3:59][O:58][C:56](=[O:57])[C@H:52]([CH:53]([CH3:54])[CH3:55])[NH:51][C:49](=[O:50])[C@H:45]([CH:46]([CH3:48])[CH3:47])[NH:44][C:22](=[O:23])[CH2:21][CH:18]1[CH2:19][CH2:20][C:14]([C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH3:13])=[CH:15][CH:16]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:17]1=[O:25]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12944632L-valyl L-valine methyl esterHCID 54027587(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 677819852-(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-1-oxo-ethyl-valinyl-valine methyl ester収率 63.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a stirred solution of the above acid (37) (1.0 g) in dimethylformamide (20 mL) was added hydroxybenzotriazole (0.62 g), HCl.Val-Val-OMe (0.67 g), triethylamine (1.93 mL) followed by Bop reagent (1.93 g). After stirring at room temperature for 16 h the reaction was evaporated to dryness and flash chromatographed on silica gel eluted with 60% ethyl acetate in n-hexane to give the titled product (38) (0.95 g, 57%). TLC Rf 0.48, 0.41 (60% ethyl acetate, n-hexane) Rf 0.40, 0.37 (97:3 CHCl3 :MeOH); MS DCI/NH3 (M+H)+ =648.5; 1H NMR (CDCl3) δ0.8-1.0(12H, m) Val γ(CH3)2 's, 1.12(3H, d, J=7 Hz) Ala CH3, 3.7(3H, s) CO2CH3, 5.1(2H, s) Cbz CH2, 5.4(1H, d) vinyl CH, 7.22(5H, s) phenyl, 7.46(5H, s) Cbz phenyl.

後処理

  1. customwas evaporated to dryness and flash
  2. customchromatographed on silica gel
  3. washeluted with 60% ethyl acetate in n-hexane

出典と根拠

ORDレコード
ord-d5ebbab86fca4bbcbf8462e531c85091
出典データセット
uspto-grants-1995_08
特許番号
US05438118

反応ノート

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