HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

11beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dione → 16alpha-(2,2-Diethoxyethoxy)-11beta,17,21-trihydroxypregn-4-ene-3,20-dione

HRID 918403
Notes
Print preview

Reaction equation

HRID 918403 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.[OH:23][C@H:24]1[CH2:44][C@@:43]2([CH3:45])[C@@H:35]([CH2:36][C@@H:37]([OH:47])[C@:38]2([OH:46])[C:39](=[O:42])[CH2:40][OH:41])[C@H:34]2[C@H:25]1[C@:26]1([CH3:49])[C:31]([CH2:32][CH2:33]2)=[CH:30][C:29](=[O:48])[CH2:28][CH2:27]1>CCOCC.CCCCC.CO>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][O:47][C@@H:37]1[CH2:36][C@@H:35]2[C@:43]([CH3:45])([CH2:44][C@H:24]([OH:23])[C@H:25]3[C@H:34]2[CH2:33][CH2:32][C:31]2[C@:26]3([CH3:49])[CH2:27][CH2:28][C:29](=[O:48])[CH:30]=2)[C@@:38]1([OH:46])[C:39](=[O:42])[CH2:40][OH:41])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10200311beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dioneHCID 1713901Urea, (2,2-diethoxyethyl)-HCID 21520892Ethane, 2-diazo-1,1-diethoxy-

Product 1

HCID 6814316216alpha-(2,2-Diethoxyethoxy)-11beta,17,21-trihydroxypregn-4-ene-3,20-dione

Reagents, catalysts & solvents 2

HCID 887Methanol
Solvent
HCID 21877078Diethylether pentaneSolvent

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 B. 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. 11β,16α,17,21-Tetrahydroxypregn-4-ene-3,20-dione, 16,17-cycloborate is added in portions until nitrogen evolution ceases. The solvent is removed in vacuo and the residue is recrystallized from methanol to yield the title compound.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-7503150db3f24ed69c50a2ca3de1ccfc
Source dataset
uspto-grants-1976_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03971773

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes