Hydrochloric Acid → HCID 66965964, compound

HRID 749102Notes

Reaction equation

HRID 749102 reaction equation
C[O:2][C:3]([CH2:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9](=[O:16])[NH:8][N:7]=1)=O.[BH4-].[Na+].Cl>O1CCCC1>[OH:2][CH2:3][CH2:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9](=[O:16])[NH:8][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 66965872HCID 66965872, compound

Product 1

HCID 66965964HCID 66965964, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The compound prepared in Example 15 (350 mg) was dissolved in tetrahydrofuran (8.0 mL). Under an atmosphere of argon, sodium borohydride (239 mg) was added thereto at 0° C. and the mixture was refluxed for 13 hours. After cooling to 0° C., 1N hydrochloric acid was added to the reaction mixture, which was adjusted to pH 5. The deposited solid was collected by filtration. The filtrate was concentrated and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and concentrated to give the title compound having the following physical data.

Workup

  1. temperatureAfter cooling to 0° C.
  2. filtrationThe deposited solid was collected by filtration
  3. concentrationThe filtrate was concentrated
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-636d4f9f48cc46648aca4e32b6e9fd57
Source dataset
uspto-grants-2008_07
Patent number
US07402580B2

Reaction notes

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