3-Amino-1,2-propanediol → HCID 10553532, compound

HRID 888747Notes

Reaction equation

HRID 888747 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[CH3:7][C@@H:8]([C@@H:15]1[C@@:19]2([CH3:37])[CH2:20][CH2:21][CH:22]3[C@@:27]4([CH3:36])[CH2:28][CH2:29][CH:30]([O:32][C:33](Cl)=[O:34])[CH2:31][C:26]4=[CH:25][CH2:24][CH:23]3[CH:18]2[CH2:17][CH2:16]1)[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[OH:6][CH:3]([CH2:4][OH:5])[CH2:2][NH:1][C:33]([O:32][C@H:30]1[CH2:29][CH2:28][C@@:27]2([CH3:36])[C:26](=[CH:25][CH2:24][C@@H:23]3[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:37])[C@H:18]3[CH2:17][CH2:16][C@@H:15]2[C@H:8]([CH3:7])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:31]1)=[O:34]

Participants

5

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 54236888C28H45ClO2

Product 1

HCID 10553532HCID 10553532, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 1140TolueneSolvent

Procedure

3-Amino-1,2-propanediol (2.0 g, 22.0 mmoles) is coevaporated twice with dry pyridine (50 mL each) then dissolved in dry pyridine (147 mL). The solution is stirred in an ice bath, and a solution of cholesteryl chloroformate (10.4 g, 23.1 mmoles) in toluene (50 mL) is added dropwise over 30 minutes. After addition, the ice bath is removed and the reaction mixture is stirred at ambient temperature for 16 hours. The solution is then evaporated, and the residue is coevaporated twice with toluene (50 mL each). The crude product is purified on silica gel (300 mL bed volume) eluting with hexanes:acetone (90:10 [v/v], 1000 mL; then 85:15 [v/v], 1000 mL; then 70:30 [v/v], 1000 mL; then 65:35 [v/v], 1000 mL). Fractions containing pure product by thin layer chromatography are pooled and evaporated to syrup which is dried well in vacuo. The yield is 5.7 g (51%).

Workup

  1. additionAfter addition
  2. customthe ice bath is removed
  3. stirringthe reaction mixture is stirred at ambient temperature for 16 hours
  4. customThe solution is then evaporated
  5. customThe crude product is purified on silica gel (300 mL bed volume)
  6. washeluting with hexanes:acetone (90:10 [v/v], 1000 mL
  7. additionFractions containing pure product by thin layer chromatography
  8. customevaporated to syrup which
  9. customis dried well in vacuo

Sources & evidence

ORD record
ord-229f7d75aad9471680e78b29dc01163d
Source dataset
uspto-grants-2012_08
Patent number
US08252755B2

Reaction notes

Loading…