Ethyl Acetate → HCID 59875629, compound

HRID 849871Notes

Reaction equation

HRID 849871 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[CH:9]=[CH:10][CH:11]([CH2:23][O:24][Si](C(C)(C)C)(C)C)[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)(C)(C)C.F.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[NH2:7][C@H:8]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)/[CH:9]=[CH:10]/[CH:11]([CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)[CH2:23][OH:24]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 14917Hydrofluoric AcidHCID 54070080HCID 54070080, compound

Product 1

HCID 59875629HCID 59875629, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

((1R)-4-(tert-Butyldimethylsilanyloxymethyl)-1-((2-naphthyl)methyl)-5-(2-naphthyl)pent-2-enyl)carbamic acid tert-butylester (2.20 g; 3.60 mmol) was dissolved in a mixture of acetonitrile (100 ml) and an aqueous solution of hydrogen fluoride (48%, 4.5 ml). After stirring for 3 h a mixture of ethyl acetate (200 ml) and aqueous sodium carbonate (10%, 200 ml) was added. The phases were separated and the organic phase was dried (Magnesium sulfate) and evaporated in vacuo. The residue was chromatographed on silica (4×38 cm) using a mixture of ethyl acetate (85%), ethanol (14%) and conc. aqueous ammonia (1%) as eluent. Two close spots were separated this way. The one that eluted first was clean on HPLC whereas the following contained several isomers. The first fraction had E-geometry and 220 mg of (3E,5R)-5-amino-6-((2-naphthyl)-2-(2-naphthyl)methyl)hex-3-en-1-ol were taken to the next step.

Workup

  1. additionwas added
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried (Magnesium sulfate)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica (4×38 cm)
  6. additiona mixture of ethyl acetate (85%), ethanol (14%) and conc. aqueous ammonia (1%) as eluent
  7. customTwo close spots
  8. customwere separated this way
  9. washThe one that eluted first was clean on HPLC whereas the

Sources & evidence

ORD record
ord-166f68915a904359a88846bde17e9244
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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