Citric Acid → HCID 86734022, compound

HRID 1576775Notes

Reaction equation

HRID 1576775 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:29][C@@:28]2([CH3:30])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:27]2[C:26](=[O:31])[CH2:25][C@@:24]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:23])[CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:6][C@@H:5]1[OH:33])[CH3:2].[C:34]([OH:46])(=[O:45])[CH2:35][C:36]([CH2:41][C:42]([OH:44])=[O:43])([C:38]([OH:40])=[O:39])[OH:37]>C(O)C>[C:34]([OH:46])(=[O:45])[CH2:35][C:36]([CH2:41][C:42]([OH:44])=[O:43])([C:38]([OH:40])=[O:39])[OH:37].[CH2:1]([O:3][C@H:4]1[CH2:29][C@@:28]2([CH3:30])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:27]2[C:26](=[O:31])[CH2:25][C@@:24]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:23])[CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:6][C@@H:5]1[OH:33])[CH3:2]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 86734023HCID 86734023, compound

Product 1

HCID 86734022HCID 86734022, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2β-ethoxy-3α-hydroxy-21-morpholino-5α-pregnane-11,20-dione (0.093 g, 0.2 mmole) in ethanol (1 ml) was treated with a 0.1M solution of citric acid (2 ml, 0.2 mmole) at room temperature. The clear solution was immediately evaporated to dryness at room temperature and redissolved in distilled water (ca. 5 ml). The aqueous solution was stored at 0° overnight and then filtered. The solid collected was washed with distilled water (ca. 1 ml) and the washings and filtrate combined. The residue was dissolved in chloroform and evaporated under vacuum to constant weight (0.0016 g). The filtrate and washings were made up to 9.14 ml with distilled water thereby giving a solution of title compound (pH 3.59) at concentration 10 mg/ml with respect to steroid.

Workup

  1. customThe clear solution was immediately evaporated to dryness at room temperature
  2. dissolutionredissolved in distilled water (ca. 5 ml)
  3. filtrationfiltered
  4. customThe solid collected
  5. washwas washed with distilled water (ca. 1 ml)
  6. dissolutionThe residue was dissolved in chloroform
  7. customevaporated under vacuum to constant weight (0.0016 g)

Sources & evidence

ORD record
ord-c2adaabddf3547158f1260d40af527ca
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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