Hydrochloric Acid → HCID 131715656, compound

HRID 1742042Notes

Reaction equation

HRID 1742042 reaction equation
FC(F)(F)C([NH:5][C@H:6]([C:26]([C:28]([C:44](=[O:72])[C@H:45]([CH2:53][C:54]1[CH:61]=[C:59]([I:60])[C:58]([O:62][C:63]2[CH:70]=[C:68]([I:69])[C:67]([OH:71])=[C:65]([I:66])[CH:64]=2)=[C:56]([I:57])[CH:55]=1)[NH:46]C(=O)C(F)(F)F)([CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][C:41]([NH2:43])=[O:42])[C:29]([NH2:31])=[O:30])=[O:27])[CH2:7][C:8]1[CH:15]=[C:13]([I:14])[C:12]([O:16][C:17]2[CH:24]=[C:22]([I:23])[C:21]([OH:25])=[C:19]([I:20])[CH:18]=2)=[C:10]([I:11])[CH:9]=1)=O.[OH-].[Na+].[ClH:77]>CO.C(O)C>[ClH:77].[ClH:77].[NH2:5][C@H:6]([C:26]([C:28]([C:44](=[O:72])[C@H:45]([CH2:53][C:54]1[CH:55]=[C:56]([I:57])[C:58]([O:62][C:63]2[CH:64]=[C:65]([I:66])[C:67]([OH:71])=[C:68]([I:69])[CH:70]=2)=[C:59]([I:60])[CH:61]=1)[NH2:46])([CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][C:41]([NH2:43])=[O:42])[C:29]([NH2:31])=[O:30])=[O:27])[CH2:7][C:8]1[CH:9]=[C:10]([I:11])[C:12]([O:16][C:17]2[CH:18]=[C:19]([I:20])[C:21]([OH:25])=[C:22]([I:23])[CH:24]=2)=[C:13]([I:14])[CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86742300HCID 86742300, compound

Product 1

HCID 131715656HCID 131715656, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Bis-(trifluoroacetyl-L-thyroxyl)-4,9-dioxadodecane-1,12-diamide (example 8A), 0.34 g, was dissolved in 3 ml methanol. 1M sodium hydroxide was added with stirring and the reaction was allowed to go at room temperature for 40 hours. The reaction mixture was diluted into 20 ml of cold 1M hydrochloric acid to give a fine suspension of product. The suspension was centrifuged and the pellet was dissolved in ethanol. The ethanol solution was evaporated to a solid residue of crude product. The product was recrystallized from methanol/ether to obtain 0.18 g of bis-(L-thyroxyl)-4,9-dioxa-1,12-dodecanediamide, dihydrochloride salt.

Workup

  1. customto give
  2. additiona fine suspension of product
  3. customThe ethanol solution was evaporated to a solid residue of crude product
  4. customThe product was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-6ec3c832e2c74392922a80ea2f04e58f
Source dataset
uspto-grants-1994_08
Patent number
US05336621

Reaction notes

Loading…