Succinic anhydride → HCID 68281999, compound

HRID 625140Notes

Reaction equation

HRID 625140 reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]([O:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH2:15][C:14]1=[CH:13][CH2:12][C@@H:11]1[C@@H:3]2[CH2:4][CH2:5][C@@:6]2([CH3:32])[C@H:10]1[CH2:9][CH2:8][C@@H:7]2[C@@H:24]([CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH3:25].CCN(C(C)C)C(C)C.CCOC(C)=O.[O:48]1[C:52](=[O:53])[CH2:51][CH2:50][C:49]1=[O:54]>C1COCC1>[CH3:25][C@@H:24]([C@@H:7]1[C@:6]2([CH3:32])[C@H:10]([C@H:11]3[C@H:3]([CH2:4][CH2:5]2)[C@:2]2([CH3:1])[C:14]([CH2:15][C@@H:16]([O:19][CH2:20][CH2:21][CH2:22][NH:23][C:52](=[O:53])[CH2:51][CH2:50][C:49]([OH:54])=[O:48])[CH2:17][CH2:18]2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)[CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 7922Succinic anhydrideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 573585901-Propanamine, 3-[(3b)-cholest-5-en-3-yloxy]-

Product 1

HCID 68281999HCID 68281999, compoundYield 114.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 2 μL round-bottomed flask, 3-((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)propan-1-amine (21.15 g, 47.7 mmol, Eq: 1.00) and Huenig's base (12.3 g, 16.6 ml, 95.3 mmol, Eq: 2.00) were combined with AcOEt (845 ml) to give a colorless solution. Dihydrofuran-2,5-dione (4.77 g, 47.7 mmol, Eq: 1.00) in THF (42 ml) was added and the reaction mixture was stirred at ambient temperature over night=>white suspension. All volatiles were removed i. v., the residue dissolved in CH2Cl2, the organic layer washed with NH4Cl and brine, dried over Na2SO4, and evaporated to dryness. The crude product was dissolved in CH3CN/H2O and lyophilized to yield 29.8 g of the title compound as fluffy powder. MS (ISP): (M−H) 542.5.

Workup

  1. customto give a colorless solution
  2. customAll volatiles were removed i
  3. dissolution, the residue dissolved in CH2Cl2
  4. washthe organic layer washed with NH4Cl and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. dissolutionThe crude product was dissolved in CH3CN/H2O

Sources & evidence

ORD record
ord-3a5c173a2ce94c38b5e3f0d2ef5d7ab5
Source dataset
uspto-grants-2016_04
Patent number
US09301990B2

Reaction notes

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