Trichloroacetic Acid → HCID 57466791, compound

HRID 2120335Notes

Reaction equation

HRID 2120335 reaction equation
[OH:1][C@@H:2]1[CH2:6][C@H:5](O)[C@H:4]([CH2:8][C:9]([OH:11])=[O:10])[C@H:3]1[CH:12]=[CH:13][C@H:14]([OH:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].CC(OC)(C)C.ClC(Cl)(Cl)C(O)=O>C(N(CC)CC)C>[OH:1][C@H:2]1[CH2:6][C@H:5]2[O:10][C:9](=[O:11])[CH2:8][C@H:4]2[C@@H:3]1/[CH:12]=[CH:13]/[C@H:14]([OH:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 15413tert-Butyl methyl etherHCID 68123490HCID 68123490, compound

Product 1

HCID 57466791HCID 57466791, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-[(1R, 2R, 3R, 5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-1-octenyl]cyclopentyl]acetic acid (XIX, EXAMPLE 11, 2.55 g) is stirred with MTBE (100 mL) and trichloroacetic acid (0.102 g). The slurry is heated to reflux for more than one hour. Then triethylamine (0.2 mL) is added. The mixture is cooled and washed once with water (50 mL) of water. The mixture is dried over anhydrous granular sodium sulfate and then concentrated under reduced pressure to give the title compound, NMR (CDCl3, 400 MHz) δ 5.58, 5.43, 4.88, 4.03, 3.92, 3.55, 2.8, 2.71, 2.3-2.5, 2.22, 1.9, 1.2-1.6 and 0.89; CMR (CDCl3, 100.6 MHz) δ 176.94, 136.79, 130.20, 82.41, 76.27, 72.78, 56.12, 42.34, 39.61, 37.05, 33.98, 31.60, 25.06, 22.52 and 13.94.

Workup

  1. temperatureThe slurry is heated
  2. temperatureto reflux for more than one hour
  3. temperatureThe mixture is cooled
  4. washwashed once with water (50 mL) of water
  5. dry with materialThe mixture is dried over anhydrous granular sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1154b792b1b940bf95a2e6cc75eb5111
Source dataset
uspto-grants-2004_02
Patent number
US06689901B2

Reaction notes

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