Hydrochloric Acid → HCID 72539640, compound

HRID 1445419Notes

Reaction equation

HRID 1445419 reaction equation
C(OC[O:5][CH:6]1[CH2:23][CH:22]2[CH:8]([C:9](=[O:36])[N:10]([CH3:35])[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][CH:17]3[C:19]([C:25]([NH:27][S:28]([C:31]4([CH3:34])[CH2:33][CH2:32]4)(=[O:30])=[O:29])=[O:26])([NH:20][C:21]2=[O:24])[CH2:18]3)[CH2:7]1)C.Cl.C(=O)([O-])O.[Na+]>C1COCC1.CO.O>[OH:5][CH:6]1[CH2:23][CH:22]2[CH:8]([C:9](=[O:36])[N:10]([CH3:35])[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][CH:17]3[C:19]([C:25]([NH:27][S:28]([C:31]4([CH3:34])[CH2:33][CH2:32]4)(=[O:30])=[O:29])=[O:26])([NH:20][C:21]2=[O:24])[CH2:18]3)[CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 72236612HCID 72236612, compound

Product 1

HCID 72539640HCID 72539640, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of the cyclopropylmethyl derivative (119) (0.38 g, 0.72 mmol) in 1:1:1 THF-methanol-H2O (6 ml) was added conc. hydrochloric acid (0.89 ml), then stirred at r for 6.5 h. The reaction mixture was then neutralized using sodium hydrogen carbonate (approx. 0.9 g solid) and concentrated into approx. half the volume. The residue was partitioned between aq. 10% citric acid (40 ml) and dichloromethane (10 ml). The water layer was washed with dichloromethane (3×10 ml), and the combined organic layers were dried (sodium sulfate), filtered and concentrated. Flash chromatography of the residue using stepwise gradient elution (methanol in ethyl acetate 5-10%) gave after concentration of the appropriate fractions the title compound as a colorless foam (0.315 g, 93%). LR-MS: Calcd for C22H34N3O6S: 468. Found: 468 [M+H].

Workup

  1. concentrationconcentrated into approx. half the volume
  2. customThe residue was partitioned between aq. 10% citric acid (40 ml) and dichloromethane (10 ml)
  3. washThe water layer was washed with dichloromethane (3×10 ml)
  4. dry with materialthe combined organic layers were dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washgradient elution (methanol in ethyl acetate 5-10%)

Sources & evidence

ORD record
ord-461d5a7f134f45dfbb72759a46b539d1
Source dataset
uspto-grants-2010_02
Patent number
US07666834B2

Reaction notes

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