Acetic Acid → HCID 71093441, compound

HRID 1472753Notes

Reaction equation

HRID 1472753 reaction equation
C(N(CC)CC)C.[CH:8]1([C:14]([OH:42])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:15]([O:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]C=O)[CH2:21][CH2:20]2)=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl.[NH2:44][CH2:45][C@@H:46]([C:48]1[CH:57]=[CH:56][C:55]([OH:58])=[C:54]2[C:49]=1[CH:50]=[CH:51][C:52](=[O:59])[NH:53]2)[OH:47].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>CO>[CH:36]1([C:14]([OH:42])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:15]([O:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:44][CH2:45][C@H:46]([OH:47])[C:48]3[CH:57]=[CH:56][C:55]([OH:58])=[C:54]4[C:49]=3[CH:50]=[CH:51][C:52](=[O:59])[NH:53]4)[CH2:21][CH2:20]2)=[O:16])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 71093241(R)-5-(2-Amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one hydrochlorideHCID 86676454HCID 86676454, compound

Product 1

HCID 71093441HCID 71093441, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (90 μL, 0.65 mmol) was added to a solution of (1-(10-oxodecyl)piperidin-4-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate (182 mg, 0.39 mmol) and (R)-5-(2-amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one hydrochloride (100 mg, 0.39 mmol) in methanol (4 mL). The reaction mixture was stirred at RT for 1 hour. Sodium triacetoxyborohydride (154 mg, 0.73 mmol) followed by acetic acid (74 μL, 1.29 mmol) were added, and the reaction mixture stirred at RT for 72 hours. The reaction was quenched with water (500 μL) and evaporated under reduced pressure. The residue was dissolved in dimethyl sulfoxide and submitted to reverse phase preparative HPLC for final purification. The title compound was isolated (42.3 mg, 16%).

Workup

  1. additionwere added
  2. stirringthe reaction mixture stirred at RT for 72 hours
  3. customThe reaction was quenched with water (500 μL)
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in dimethyl sulfoxide
  6. custompurification

Sources & evidence

ORD record
ord-25b2b20d07e640af894bfb625f007d16
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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