Methanol → HCID 67170000, compound

HRID 1918288Notes

Reaction equation

HRID 1918288 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-aea3b03c4db24a52bb9ff38f01e04d63
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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