Citric Acid → HCID 131721281, compound

HRID 1416530Notes

Reaction equation

HRID 1416530 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@@H:11]([C@@H:12]([OH:29])[CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[OH:28])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:30]([O:32][CH2:33]Cl)[CH3:31].C(N([CH:41]([CH3:43])C)CC)(C)C.C(O)(=O)C[C:46](CC(O)=O)(C(O)=O)[OH:47]>ClCCl>[Si:1]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@@H:11]([C@@H:12]([O:29][CH2:46][O:47][CH2:41][CH3:43])[CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[O:28][CH2:33][O:32][CH2:30][CH3:31])[CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 70048397HCID 70048397, compound

Product 1

HCID 131721281HCID 131721281, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3β-tert-butyldimethylsilyloxy-5α-androstan-6α,17β-diol (II-a, Prep. 1, 10 g), chloromethyl ethyl ether (16 mL) and di-iso-propylethylamine (120 mL) in dry dichloromethane (500 mL) was stirred overnight at 0° C. Citric acid (10% water solution, 1.5 L) was added, the organic layer separated, washed with water and dried over anhydrous sodium sulfate. The solvent was removed in vacuo. The residue was purified by chromatography (hexane/ethyl acetate 85/15) to give 10.8 g of 3β-tert-butyldimethylsilyloxy-6α,17β-di-ethoxymethoxy-5α-androstane. 1H-NMR (300 MHz, CDCl3, ppm from TMS): 4.60 (4H, m), 3.70-3.40 (7H, m), 2.20-0.6 (41H, m), 0.03 (6H, s).

Workup

  1. customthe organic layer separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by chromatography (hexane/ethyl acetate 85/15)

Sources & evidence

ORD record
ord-cb37d465c19240f2a4f7953300f0960c
Source dataset
uspto-grants-1999_06
Patent number
US05914324

Reaction notes

Loading…