Glycine → N-(cholest-5-en-3beta-oxycarbonyl)glycine

HRID 465292Notes

Reaction equation

HRID 465292 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].C(N(CC)CC)C.O1CCOCC1.[CH3:19][C@@H:20]([C@@H:27]1[C@@:31]2([CH3:49])[CH2:32][CH2:33][CH:34]3[C@@:39]4([CH3:48])[CH2:40][CH2:41][CH:42]([O:44][C:45](Cl)=[O:46])[CH2:43][C:38]4=[CH:37][CH2:36][CH:35]3[CH:30]2[CH2:29][CH2:28]1)[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25]>O>[CH3:26][CH:24]([CH2:23][CH2:22][CH2:21][C@H:20]([C@@H:27]1[C@:31]2([CH3:49])[C@H:30]([C@H:35]3[C@H:34]([CH2:33][CH2:32]2)[C@:39]2([CH3:48])[C:38]([CH2:43][C@@H:42]([O:44][C:45]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:46])[CH2:41][CH2:40]2)=[CH:37][CH2:36]3)[CH2:29][CH2:28]1)[CH3:19])[CH3:25]

Participants

6

Reactant 4

HCID 750GlycineHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 54236888C28H45ClO2

Product 1

HCID 14168269N-(cholest-5-en-3beta-oxycarbonyl)glycineYield 68.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of glycine (1.50 g) in water (100 ml) was added triethylamine (4.04 g). After dioxan (200 ml) and cholesteryl chloroformate (8.98 g) were added to the resulting clear solution at 0° C., the mixture was stirred for 3 hours. The reaction mixture was concentrated under reduced pressure and, 1 N hydrochloric acid (23 ml) and chloroform (100 ml) were added to the residue. The organic phase was separated and washed with water and then dried over magnesium sulfate. The solvent was distilled off to give crude crystals. After washing with ethanol, the crystals were filtered to give N-(cholest-5-ene-3β-oxycarbonyl)glycine (6.64 g) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and, 1 N hydrochloric acid (23 ml) and chloroform (100 ml)
  2. additionwere added to the residue
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customto give crude crystals
  8. washAfter washing with ethanol
  9. filtrationthe crystals were filtered

Sources & evidence

ORD record
ord-9fb24ae437c640f8836a60eaed3e142d
Source dataset
uspto-grants-1992_10
Patent number
US05152999

Reaction notes

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