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 1755818노트

반응식

HRID 1755818 반응식
[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]

참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d5ebbab86fca4bbcbf8462e531c85091
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05438118

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