Water → (3beta,5beta,7alpha,12alpha)-3-(9H-Fluoren-9-ylmethoxy)amino-7,12-dihydroxycholan-24-oic acid

HRID 2264101Notes

Reaction equation

HRID 2264101 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][C@@H:24]([OH:47])[C@@H:25]3[C@@H:40]2[CH2:39][C@H:38]([OH:45])[C@@:37]2([CH3:46])[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][C@@H:24]([OH:47])[C@@H:25]5[C@@H:40]4[CH2:39][C@H:38]([OH:45])[C@@:37]4([CH3:46])[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 540188313beta-amino-7alpha,12alpha-dihydroxy-5beta-cholan-24-oic Acid

Product 1

HCID 86595425(3beta,5beta,7alpha,12alpha)-3-(9H-Fluoren-9-ylmethoxy)amino-7,12-dihydroxycholan-24-oic acidYield 71%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 9-fluorenylmethoxycarbonyl chloride (1.4 g; 5.4 mmol) in 1,4-dioxane (18 mL) was added dropwise to a suspension of (3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid A (2.0 g; 4.9 mmol) (3) in 10% aq. Na2CO3 (30 mL) and 1,4-dioxane (18 mL) stirred at 0° C. After 6 h stirring at room temperature H2O (100 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 precipitated solid was filtered, washed with H2O (3×100 mL), vacuum dried and then purified by flash chromatography to give B as a white solid (2.2 g; 3.5 mmol). Yield 71%.

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. filtrationThe precipitated solid was filtered
  5. washwashed with H2O (3×100 mL), vacuum
  6. customdried
  7. custompurified by flash chromatography
  8. customto give B as a white solid (2.2 g; 3.5 mmol)

Sources & evidence

ORD record
ord-e559f21210934a90850df0d303acb3eb
Source dataset
uspto-grants-2010_12
Patent number
US07850947B2

Reaction notes

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