Hydrochloric Acid → HCID 178502915, compound

HRID 1614903Notes

Reaction equation

HRID 1614903 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([O-:12])=[O:11])=[C:7]([N:13]([CH:23]2[CH2:28][CH2:27][P:26]([O:30][CH3:31])(=[O:29])[CH2:25][CH2:24]2)[C:14]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH3:22])[CH2:18][CH2:17]2)=[O:15])[CH:6]=1.[Li+].[OH-].Cl>CO.C1COCC1>[CH3:32][C:2]([CH3:1])([CH3:33])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([CH:23]2[CH2:28][CH2:27][P:26]([O:30][CH3:31])(=[O:29])[CH2:25][CH2:24]2)[C:14]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH3:22])[CH2:18][CH2:17]2)=[O:15])[CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178502914HCID 178502914, compound

Product 1

HCID 178502915HCID 178502915, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(3,3-Dimethyl-but-1-ynyl)-3-[(1-methoxy-1-oxo-1λ5-phosphinan-4-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylate (36 mg, 0.07 mmol) was dissolved in 1 mL of methanol and 1 mL of THF, and to the solution was added 0.2 mL of 1 N LiOH. The reaction mixture was stirred at room temperature for 5 hours, and then cooled to 0° C. and neutralized with 0.4 mL of 0.5 N HCl. After removal of solvent, the residue was purified by HPLC (Gemini column; 5% acetonitrile:water, 5 min; 5-100% acetonitrile:water, 18 min; 100% acetonitrile, 6 min; both solvents containing 0.1% trifluoroacetic acid), resulting in 20 mg (57%) of the title compound. MS (m/z): 494.2 [M+H]+; HPLC retention time: 4.144 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Workup

  1. customAfter removal of solvent
  2. customthe residue was purified by HPLC (Gemini column
  3. customwater, 5 min
  4. customwater, 18 min
  5. custom100% acetonitrile, 6 min
  6. additionboth solvents containing 0.1% trifluoroacetic acid),

Sources & evidence

ORD record
ord-2c8c6b6477584815886de7fed8701a5a
Source dataset
uspto-grants-2014_07
Patent number
US08765722B2

Reaction notes

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