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

HRID 2292323

Reaction equation

HRID 2292323 reaction equation
C([O:4][C:5]1[C:42]([CH2:43][N:44]([CH2:53][C:54]([O:56]C(C)(C)C)=[O:55])[CH2:45][C:46]([O:48]C(C)(C)C)=[O:47])=[CH:41][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH:18]([C:37]([O:39][CH3:40])=[O:38])[C:19]3[CH:24]=[C:23]([I:25])[C:22]([O:26][C:27]4[CH:32]=[C:31]([I:33])[C:30]([OH:34])=[C:29]([I:35])[CH:28]=4)=[C:21]([I:36])[CH:20]=3)[CH:12]=2)=[O:10])=[CH:7][C:6]=1[CH2:61][N:62]([CH2:71][C:72]([O:74]C(C)(C)C)=[O:73])[CH2:63][C:64]([O:66]C(C)(C)C)=[O:65])(=O)C>FC(F)(F)C(O)=O.O>[C:64]([CH2:63][N:62]([CH2:61][C:6]1[CH:7]=[C:8]([CH:41]=[C:42]([CH2:43][N:44]([CH2:53][C:54]([OH:56])=[O:55])[CH2:45][C:46]([OH:48])=[O:47])[C:5]=1[OH:4])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH:18]([C:37]([O:39][CH3:40])=[O:38])[C:19]2[CH:24]=[C:23]([I:25])[C:22]([O:26][C:27]3[CH:32]=[C:31]([I:33])[C:30]([OH:34])=[C:29]([I:35])[CH:28]=3)=[C:21]([I:36])[CH:20]=2)[CH:12]=1)=[O:10])[CH2:71][C:72]([OH:74])=[O:73])([OH:66])=[O:65]

Participants

4

Reactant 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

Product 1

HCID 538207413,5-bis[N,N-bis(carboxymethyl)aminomethyl]-4-hydroxy-3'-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo-beta-methoxycarbonylphenethyl]benzophenone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 630 mg of 21 in 5 mL of trifluoroacetic acid was stirred overnight, diluted with water and the solid which separated was collected and dried; yield 550 mg. The field desorption mass spectrum showed 22 (m/e1305) is present, as well as some material in which the methyl ester of the thyroxine has been hydrolyzed to the acid.

Workup

  1. customthe solid which separated
  2. customwas collected
  3. customdried

Sources & evidence

ORD record
ord-8a7b1a651baa4cb6b892f66da1eb9a84
Source dataset
uspto-grants-1989_01
Patent number
US04801722

Linked notes

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