Tixocortol → 21-[2-(Formylamino)-4-methylthio-1-oxobutylthio]-11beta,17-dihydroxy-pregna-4-ene-3,20-dione

HRID 1196827Notes

Reaction equation

[OH:1][C@H:2]1[CH2:22][C@@:21]2([CH3:23])[C@@H:13]([CH2:14][CH2:15][C@:16]2([OH:24])[C:17](=[O:20])[CH2:18][SH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:26])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:25])[CH2:6][CH2:5]1.[CH:27]([NH:29][C@H:30]([C:35](O)=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28]>>[CH:27]([NH:29][CH:30]([CH2:31][CH2:32][S:33][CH3:34])[C:35](=[O:36])[S:19][CH2:18][C:17](=[O:20])[C@:16]1([OH:24])[C@:21]2([CH3:23])[C@H:13]([C@H:12]3[C@H:3]([C@@H:2]([OH:1])[CH2:22]2)[C@:4]2([CH3:26])[C:9](=[CH:8][C:7](=[O:25])[CH2:6][CH2:5]2)[CH2:10][CH2:11]3)[CH2:14][CH2:15]1)=[O:28]

Participants

Reactant 2

HCID 162955Tixocortol

HCID 439750N-Formylmethionine

Product 1

HCID 8839532421-[2-(Formylamino)-4-methylthio-1-oxobutylthio]-11beta,17-dihydroxy-pregna-4-ene-3,20-dioneYield 26.7%

Procedure

The title compound (0.38 gm) was prepared from 11β,17-dihydroxy-pregna-4-ene-3,20-dione-21-thiol (1.00 gm) and N-formyl-L-methionine (1.41 gm) in the same manner as in Synthetic Example 1.

Sources & evidence

ORD record: ord-0f36832065574788b46c17bfd034e6c2
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05116829

Reaction notes

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