Diethylenetriaminepentaacetic acid → HCID 88176279、化合物

HRID 990030

反応式

HRID 990030 の反応式
C[O:2][C:3](=[O:23])[C@H:4]([CH2:6][C:7]1[CH:12]=[C:11]([I:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[C:9]([I:22])[CH:8]=1)[NH2:5].CC([O:28][C:29](=[O:75])[C@H:30]([CH2:70][CH2:71][C:72](O)=[O:73])[N:31]([CH2:51][CH2:52][N:53]([CH2:62][C:63]([O:65]C(C)(C)C)=[O:64])[CH2:54][C:55](=[O:61])[O:56]C(C)(C)C)[CH2:32][CH2:33][N:34]([CH2:43][C:44](=[O:50])[O:45]C(C)(C)C)[CH2:35][C:36](=[O:42])[O:37]C(C)(C)C)(C)C.N[C@H](C(O)=O)CCC(O)=O.N[C@H](C(O)=O)CCCCN.C(N(CC(O)=O)CCN(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C(P(C#N)(CC)=O)C.C(N(C(C)C)C(C)C)C>CN(C=O)C>[C:44]([CH2:43][N:34]([CH2:35][C:36]([OH:42])=[O:37])[CH2:33][CH2:32][N:31]([CH2:51][CH2:52][N:53]([CH2:62][C:63]([OH:65])=[O:64])[CH2:54][C:55]([OH:61])=[O:56])[CH:30]([C:29]([OH:75])=[O:28])[CH2:70][CH2:71][C:72]([NH:5][C@H:4]([C:3]([OH:2])=[O:23])[CH2:6][C:7]1[CH:12]=[C:11]([I:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[C:9]([I:22])[CH:8]=1)=[O:73])([OH:50])=[O:45]

参加物

9

反応物 7

HCID 3053Diethylenetriaminepentaacetic acidHCID 5962L-LysineHCID 33032L-Glutamic AcidHCID 81531DiisopropylethylamineHCID 13586794DiethylphosphorylcyanideHCID 14011739o-(4-Hydroxyphenyl)-3,5-diiodo-l-tyrosine methyl esterHCID 54314119N,N-bis[2-[bis [2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-l-glutamic acid 1-(1,1-dimethylethyl) ester

生成物 1

HCID 88176279HCID 88176279、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

O-(4-Hydroxyphenyl)-3,5-diiodo-L-tyrosine methyl ester, prepared according to Example 4 Step A, was reacted with N,N-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-L-glutamic acid 1-(1,1-dimethyl-ethyl) ester (prepared according to: Anelli P. L., Fedeli F., Gazzotti O., Lattuada L., Lux G. and Rebasti F., “L-Glutamic Acid and L-Lysine as Useful Building Blocks for the Preparation of Bifuctional DTPA-like Ligand”, Bioconjugate Chem. (1999), 10, 137-140), diethylphosphoryl cyanide (DEPC) and ethyldiisopropylamine (DIEA), in DMF, under nitrogen atmosphere at 0° C. After purification by flash chromatography, the pentaester was deprotected at first with TFA in CH2Cl2 at room temperature for 47 h, then with 2 M LiOH for 21 h. The solution was acidified to pH 3.3 with aq. HCl and loaded onto an Amberlite® XAD 1600 resin column. Eluting with a H2O/CH3CN gradient afforded the ligand.

後処理

  1. customprepared
  2. customat 0° C
  3. customAfter purification by flash chromatography
  4. customat room temperature
  5. customfor 47 h
  6. washEluting with a H2O/CH3CN
  7. customgradient afforded the ligand

出典と根拠

ORDレコード
ord-1a55c2c4c2d148dc890195edd49b2e33
出典データセット
uspto-grants-2002_10
特許番号
US06458337B1

関連ノート

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