Triethylamine → (3beta,5beta,7alpha,12alpha)-3-(1-Oxopent-4-enyl)amino-7,12-dihydroxy-cholan-24-oic acid methyl ester

HRID 266024Notes

Reaction equation

HRID 266024 reaction equation
[C:1](O)(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:23][O:24][C:25](=[O:52])[CH2:26][CH2:27][C@H:28]([C@@H:30]1[C@:47]2([CH3:48])[C@H:33]([C@H:34]3[C@H:44]([CH2:45][C@@H:46]2[OH:49])[C@:42]2([CH3:43])[C@@H:37]([CH2:38][C@@H:39]([NH2:50])[CH2:40][CH2:41]2)[CH2:36][C@H:35]3[OH:51])[CH2:32][CH2:31]1)[CH3:29]>C1COCC1>[CH3:23][O:24][C:25](=[O:52])[CH2:26][CH2:27][C@H:28]([C@@H:30]1[C@:47]2([CH3:48])[C@H:33]([C@H:34]3[C@H:44]([CH2:45][C@@H:46]2[OH:49])[C@:42]2([CH3:43])[C@@H:37]([CH2:38][C@@H:39]([NH:50][C:1](=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5])[CH2:40][CH2:41]2)[CH2:36][C@H:35]3[OH:51])[CH2:32][CH2:31]1)[CH3:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 611384-Pentenoic acidHCID 62365Isobutyl chloroformateHCID 10364902HCID 10364902, compound

Product 1

HCID 54437505(3beta,5beta,7alpha,12alpha)-3-(1-Oxopent-4-enyl)amino-7,12-dihydroxy-cholan-24-oic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-pentenoic acid (marketed product) and triethylamine in THF was added drop by drop, under nitrogen and at 5° C., to isobutyl chloroformate and subsequently with a solution of (3β,5β,7α,12α)-3-amino-7,12-dihydroxy-cholan-24-oic acid methyl ester (prepared according to the procedure described in EXAMPLE 5) in THF. When the reaction was over, solvent was evaporated and the residue was taken up with H2O and AcOEt. The organic phase was separated, washed with H2O, dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by flash chromatography to obtain the desired product.

Workup

  1. customwas evaporated
  2. customThe organic phase was separated
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-348cfa841ead497595c808489a63437d
Source dataset
uspto-grants-1997_07
Patent number
US05649537

Reaction notes

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