Hydrochloric Acid → HCID 44479771, compound

HRID 2235070Notes

Reaction equation

HRID 2235070 reaction equation
[OH-].[Na+].CO.[CH3:5][O:6][C:7]([C:9]1[S:10][C:11]([CH2:14][CH2:15][CH2:16][C@H:17]2[CH2:21][CH2:20][C:19]([Cl:22])=[C:18]2[C:23]2[CH:28]=[CH:27][C:26]([C@H:29]([O:35]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:25][CH:24]=2)=[CH:12][CH:13]=1)=[O:8].Cl>C1COCC1>[CH3:5][O:6][C:7]([C:9]1[S:10][C:11]([CH2:14][CH2:15][CH2:16][C@H:17]2[CH2:21][CH2:20][C:19]([Cl:22])=[C:18]2[C:23]2[CH:24]=[CH:25][C:26]([C@H:29]([OH:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:27][CH:28]=2)=[CH:12][CH:13]=1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23721981Sodium hydroxide methanolHCID 44479772HCID 44479772, compound

Product 1

HCID 44479771HCID 44479771, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5% NaOH/MeOH (0.25 mL, 0.31 mmol), ester 14 (18 mg, 0.029 mmol) and THF (0.05 mL) was allowed to stir at room temperature. After 30 min., 10 mL 1 M HCl solution was added and the resulting mixture was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate solution was dried (MgSO4), filtered and evaporated. Purification by flash chromatography on silica gel (0%→50% ethyl acetate/hexanes) gave compound 15 (11 mg, 0.024 mmol, 82%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (2×20 mL)
  2. dry with materialThe combined ethyl acetate solution was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography on silica gel (0%→50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-63d2c353fd254c3c827d6aebdcbc64fa
Source dataset
uspto-grants-2010_05
Patent number
US07713968B2

Reaction notes

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