Hydrochloric Acid → HCID 59536869, compound

HRID 2402807Notes

Reaction equation

HRID 2402807 reaction equation
[Cl-].[Li+].[BH4-].[Na+].[C:5]([O:9][C:10]([NH:12][CH:13]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([F:27])[F:26])[CH:20]=1)[C:14](OCC)=[O:15])=[O:11])([CH3:8])([CH3:7])[CH3:6].Cl>C(O)C.O1CCCC1>[F:26][CH:25]([F:27])[C:21]1[CH:20]=[C:19]([CH:13]([NH:12][C:10](=[O:11])[O:9][C:5]([CH3:6])([CH3:8])[CH3:7])[CH2:14][OH:15])[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 59536824HCID 59536824, compound

Product 1

HCID 59536869HCID 59536869, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

At RT, 11.97 mg (0.28 mmol) of lithium chloride and 10.68 mg (0.28 mmol) of sodium borohydride were stirred in 0.25 ml of ethanol for 15 min. Then the mixture was cooled to 0° C. and a solution of 62 mg (about 0.09 mmol, purity 49%) of the compound from Example 131A in 0.25 ml of tetrahydrofuran was added dropwise. The mixture was stirred overnight at RT. For work-up, it was cooled with ice-water and adjusted to a pH of 2 using 1M hydrochloric acid. The reaction mixture was purified by preparative HPLC [Method 20]. The product fraction was freed from the solvent on a rotary evaporator and dried in an HV. This gave 56 mg (about 45% purity, 93% of theory) of the title compound.

Workup

  1. customThe reaction mixture was purified by preparative HPLC [Method 20]
  2. customThe product fraction was freed from the solvent on a rotary evaporator
  3. customdried in an HV

Sources & evidence

ORD record
ord-47cd5bc7819e419f81e1ef072c1f4cac
Source dataset
uspto-grants-2014_08
Patent number
US08796324B2

Reaction notes

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