Lithium Hydroxide → HCID 11545923, compound

HRID 2243501Notes

Reaction equation

HRID 2243501 reaction equation
C[O:2][C:3]([C:5]1[S:23][C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([NH:16][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[C:14]=3[S:15][C:7]=2[C:6]=1[O:24][CH2:25][C:26]([O:28]CC)=[O:27])=[O:4].[Li+].[OH-]>C1COCC1.O>[C:26]([CH2:25][O:24][C:6]1[C:7]2[S:15][C:14]3[C:13]([NH:16][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[CH:12][CH:11]=[CH:10][C:9]=3[C:8]=2[S:23][C:5]=1[C:3]([OH:4])=[O:2])([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68547352HCID 68547352, compound

Product 1

HCID 11545923HCID 11545923, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Step C Hydrolysis: To a solution of 7-Cyclohexylamino-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester (30 mg, 0.07 mmol) in THF/H2O (1.5 mL/0.5 mL) was added 2.0M LiOH (0.15 mL, 0.35 mmol). The reaction was allowed to stir at ambient temperature over a 16-hour period, after which it was judged complete by LCMS. The THF was removed in vacuo and the resultant aqueous solution was acidified to pH ˜1-2 using 10% HCl to precipitate the desired compound which was filtered, rinsed with water, and oven-dried (55° C.). No purification was necessary. (Yield=20 mg, 71%)

Workup

  1. customStep C Hydrolysis
  2. customThe THF was removed in vacuo
  3. customto precipitate the desired compound which
  4. filtrationwas filtered
  5. washrinsed with water
  6. customoven-dried (55° C.)
  7. customNo purification

Sources & evidence

ORD record
ord-bb742a711a144f0aab7585e3a0d2914f
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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