Hydrochloric Acid → HCID 86585317, compound

HRID 1358888Notes

Reaction equation

HRID 1358888 reaction equation
C([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][C@@H:18]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][S:32]([CH2:35][CH2:36][CH2:37][C:38]([F:44])([F:43])[C:39]([F:42])([F:41])[F:40])(=[O:34])=[O:33])([CH3:16])[C@@H:14]([O:45][C:46](=[O:48])[CH3:47])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=O)C.O.C(=O)(O)[O-].[K+].Cl>CO>[C:46]([O:45][C@H:14]1[CH2:13][CH2:12][C@H:11]2[C@H:10]3[C@H:19]([C@@H:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][S:32]([CH2:35][CH2:36][CH2:37][C:38]([F:43])([F:44])[C:39]([F:40])([F:41])[F:42])(=[O:33])=[O:34])[CH2:17][C@:15]12[CH3:16])[C:20]1[CH:21]=[CH:22][C:5]([OH:4])=[CH:6][C:7]=1[CH2:8][CH2:9]3)(=[O:48])[CH3:47]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 516893Potassium BicarbonateHCID 21138126HCID 21138126, compound

Product 1

HCID 86585317HCID 86585317, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.37 g of the diacetate obtained in Example 93 in 27.5 cm3 of methanol with 10% water is cooled down to 0° C. and 203 mg of potassium bicarbonate is added, the reaction medium is left to return to ambient temperature and agitation is carried out for 19 hours. The reaction medium is poured into 220 cm3 of water with 55 cm3 of 0.1N hydrochloric acid added to it, extracted with ethyl acetate, dried and the solvent is evaporated off. The residue is chromatographed on silica (eluant: ethyl acetate-cyclohexane 35-65) then the residue is crystallized from a methylene chloride/isopropyl ether mixture. 973 mg of expected product is obtained. M.p.=130° C.

Workup

  1. waitthe reaction medium is left
  2. customto return to ambient temperature
  3. additionadded to it
  4. extractionextracted with ethyl acetate
  5. customdried
  6. customthe solvent is evaporated off
  7. customThe residue is chromatographed on silica (eluant: ethyl acetate-cyclohexane 35-65)
  8. customthe residue is crystallized from a methylene chloride/isopropyl ether mixture

Sources & evidence

ORD record
ord-60d11a2b61d642f2ac3a62b741869b75
Source dataset
uspto-grants-2003_07
Patent number
US06596885B2

Reaction notes

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