Water → (3beta,5beta)-3-(9H-Fluoren-9-ylmethoxy)aminocholan-24-oic acid

HRID 2264085Notes

Reaction equation

HRID 2264085 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15]C(Cl)=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:19][C@H:20]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C@H:22]([CH2:23][CH2:24][C@@H:25]3[C@@H:40]2[CH2:39][CH2:38][C@@:37]2([CH3:45])[C@H:26]3[CH2:27][CH2:28][C@@H:29]2[C@H:30]([CH3:36])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH2:21]1.O>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][NH:19][C@H:20]3[CH2:43][CH2:42][C@@:41]4([CH3:44])[C@H:22]([CH2:23][CH2:24][C@@H:25]5[C@@H:40]4[CH2:39][CH2:38][C@@:37]4([CH3:45])[C@H:26]5[CH2:27][CH2:28][C@@H:29]4[C@H:30]([CH3:36])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH2:21]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 343679-Fluorenylmethyl chloroformateHCID 23391053HCID 23391053, compound

Product 1

HCID 86595424(3beta,5beta)-3-(9H-Fluoren-9-ylmethoxy)aminocholan-24-oic acidYield 69%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 9-fluorenylmethoxycarbonyl chloride (0.76 g; 2.93 mmol) in 1,4-dioxane (9 mL) was added dropwise to a suspension of (3β,5β)-3-aminocholan-24-oic acid B (1.0 g; 2.66 mmol) in 10% aq. Na2CO3 (16 mL) and 1,4-dioxane (9 mL) stirred at 0° C. After 6 h stirring at room temperature H2O (90 mL) was added, the aqueous phase washed with Et2O (2×90 mL) and then 2 M HCl (15 mL) was added (final pH: 1.5). The aqueous phase was extracted with EtOAc (2×100 mL), the organic phase dried over Na2SO4 and evaporated. The crude was purified by flash chromatography to give C as a white solid (1.2 g; 2.0 mmol). Yield 69%.

Workup

  1. additionwas added
  2. washthe aqueous phase washed with Et2O (2×90 mL)
  3. addition2 M HCl (15 mL) was added (final pH: 1.5)
  4. extractionThe aqueous phase was extracted with EtOAc (2×100 mL)
  5. dry with materialthe organic phase dried over Na2SO4
  6. customevaporated
  7. customThe crude was purified by flash chromatography
  8. customto give C as a white solid (1.2 g; 2.0 mmol)

Sources & evidence

ORD record
ord-d757c73ceeac44559c43025da4ee0cab
Source dataset
uspto-grants-2010_12
Patent number
US07850947B2

Reaction notes

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