Methanol → HCID 67170000, compound

HRID 1475699Notes

Reaction equation

HRID 1475699 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:13][C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH:16]=2)[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[CH2:7][CH2:6]1)=[O:4].[BH4-].[Na+].CO>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([NH:13][C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH:16]=2)[CH2:11][CH2:10][CH2:9][CH:8]([OH:12])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 67169932HCID 67169932, compound

Product 1

HCID 67170000HCID 67170000, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of step 1 (67 mg, 0.148 mmol) was dissolved in THF (1 ml) and cooled in an ice bath. Sodium borohydride (5.7 mg, 0.148 mmol) was added. Subsequently methanol (0.3 ml) was added dropwise. The ice bath was removed and after stirring for 45 min at room temperature the mixture was partitioned between EA and 2 N hydrochloric acid. The aqueous phase was extracted with EA, and the combined organic phases were dried over sodium sulfate and evaporated to dryness to yield the title compound (65 mg).

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice bath was removed
  3. customwas partitioned between EA and 2 N hydrochloric acid
  4. extractionThe aqueous phase was extracted with EA
  5. dry with materialthe combined organic phases were dried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-cbdadc05d8ef4cbc93ea378ee7d03152
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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