Succinic anhydride → Thyroxine

HRID 279819

Reaction equation

HRID 279819 reaction equation
O1CCCC1.C(N(CC)CC)C.C1(=O)OC(=O)CC1.Cl.C[O:22][C:23](=[O:45])[C@H:24]([CH2:26][C:27]1[CH:34]=[C:32]([I:33])[C:31]([O:35][C:36]2[CH:43]=[C:41]([I:42])[C:40]([OH:44])=[C:38]([I:39])[CH:37]=2)=[C:29]([I:30])[CH:28]=1)[NH2:25]>>[NH2:25][C@H:24]([C:23]([OH:45])=[O:22])[CH2:26][C:27]1[CH:28]=[C:29]([I:30])[C:31]([O:35][C:36]2[CH:37]=[C:38]([I:39])[C:40]([OH:44])=[C:41]([I:42])[CH:43]=2)=[C:32]([I:33])[CH:34]=1

Participants

5

Reactant 4

HCID 7922Succinic anhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13911220Methyl thyroxinate hydrochloride

Product 1

HCID 5819Thyroxine

Conditions

Temperature
4 °C

Procedure

In 150 ml of dried tetrahydrofuran 1.65 g (0.002 mol) of thyroxine methyl ester hydrochloride was dissolved. To the resulting solution 300 μl (0.0021 mol) of triethyl amine and 200 mg. (0.0022 mol) of succinic anhydride were added. The mixture was stirred at 4° C. overnight to effect reaction.

Workup

  1. customreaction

Sources & evidence

ORD record
ord-d6e33fbb8e70494a89adc8bd3b8100b1
Source dataset
uspto-grants-1986_05
Patent number
US04587102

Linked notes

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