Urea, (2,2-diethoxyethyl)- → 21-Chloro-16alpha-(2,2-diethoxyethoxy)-11beta,17-dihydroxypregna-1,4-diene-3,20-dione

HRID 918405Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH:5]=[N+]=[N-])[CH3:2].C(OC(OCC)CNC(N)=O)C.[Cl:23][CH2:24][C:25](=[O:49])[C@:26]1([OH:48])[C@:43]2([CH3:44])[C@H:29]([C@H:30]3[C@H:40]([C@@H:41]([OH:45])[CH2:42]2)[C@:38]2([CH3:39])[C:33](=[CH:34][C:35](=[O:46])[CH:36]=[CH:37]2)[CH2:32][CH2:31]3)[CH2:28][C@H:27]1[OH:47]>CO>[Cl:23][CH2:24][C:25](=[O:49])[C@:26]1([OH:48])[C@:43]2([CH3:44])[C@H:29]([C@H:30]3[C@H:40]([C@@H:41]([OH:45])[CH2:42]2)[C@:38]2([CH3:39])[C:33](=[CH:34][C:35](=[O:46])[CH:36]=[CH:37]2)[CH2:32][CH2:31]3)[CH2:28][C@H:27]1[O:47][CH2:5][CH:4]([O:8][CH2:9][CH3:10])[O:3][CH2:1][CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2,2-diethoxy-1-diazoethane (prepared from 0.0935 mole of N-2,2-diethoxyethyl urea by the method of W. Kirmse and M. Buschhoff, Chem. Ber., 100, 1491 (1967)) in 300 ml of 3:2 ether-pentane is diluted with 100 ml of methanol and cooled to 0°C. 21-Chloro-11β,16α,17-trihydroxypregna-1,4-diene-3,20-dione, 16,17-cycloborate is added in portions until nitrogen evolution ceases. The solvent is removed in vacuo to yield the title compound.

Workup

customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-2d813c81b2a043a78d6f4aae31eea7e8
Source dataset: uspto-grants-1976_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03971773

Reaction notes

Loading…