Thyroxine → 4-Acetoxy-3,5-bis[N,N-bis(t-butoxycarbonylmethyl)aminomethyl]-3'-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo-beta-methoxycarbonylphenethyl]benzophenone

HRID 652338

반응식

HRID 652338 반응식
[C:1]([O:4][C:5]1[C:21]([CH2:22][N:23]([CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:20][C:8]([C:9](C2C=CC=C(C(O)=O)C=2)=[O:10])=[CH:7][C:6]=1[CH2:40][N:41]([CH2:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])(=[O:3])[CH3:2].C(N1[C:72]2[C:67](=[CH:68][CH:69]=[CH:70][CH:71]=2)[CH:66]=[CH:65][CH:64]1[O:73][CH2:74]C)(OCC)=O.N[C@H](C(O)=O)C[C:79]1[CH:86]=[C:84]([I:85])[C:83]([O:87][C:88]2[CH:95]=[C:93]([I:94])[C:92]([OH:96])=[C:90]([I:91])[CH:89]=2)=[C:81]([I:82])[CH:80]=1.[O:100]1CCCC1>>[C:1]([O:4][C:5]1[C:21]([CH2:22][N:23]([CH2:32][C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[CH2:24][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])=[CH:20][C:8]([C:9]([C:71]2[CH:70]=[CH:69][CH:68]=[C:67]([CH2:66][CH:65]([C:64]([O:73][CH3:74])=[O:100])[C:79]3[CH:86]=[C:84]([I:85])[C:83]([O:87][C:88]4[CH:89]=[C:90]([I:91])[C:92]([OH:96])=[C:93]([I:94])[CH:95]=4)=[C:81]([I:82])[CH:80]=3)[CH:72]=2)=[O:10])=[CH:7][C:6]=1[CH2:40][N:41]([CH2:42][C:43]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:44])[CH2:50][C:51]([O:53][C:54]([CH3:55])([CH3:56])[CH3:57])=[O:52])(=[O:3])[CH3:2]

참가 물질

5

반응물 4

HCID 5819ThyroxineHCID 8028TetrahydrofuranHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 144055134-Acetoxy-3,5-bis[N,N-bis(t-butoxycarbonylmethyl)aminomethyl]-3'-carboxybenzophenone

생성물 1

HCID 867415754-Acetoxy-3,5-bis[N,N-bis(t-butoxycarbonylmethyl)aminomethyl]-3'-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo-beta-methoxycarbonylphenethyl]benzophenone

실험 절차

A mixture of 900 mg of 20 and 0.265 g (1.07 mmol) of 1-carbethoxy-2-ethoxy-1,2-dihydroquinoline (EEDQ) in 20 mL of dry tetrahydrofuran was stirred for 30 minutes and 0.85 g (1.07 mmol) of the methyl ester of thyroxine was added. The mixture was stirred overnight. The reaction mixture was purified by gel permeation chromatography using tetrahydrofuran as the solvent, giving 630 mg of material which showed an NMR spectrum which was consistent with structure 21.

후처리

  1. stirringThe mixture was stirred overnight
  2. customThe reaction mixture was purified by gel permeation chromatography

출처 및 근거

ORD 기록
ord-f878abf85d13455ab7f6ab28dc2766d4
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04670572

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