Methanol → HCID 67076718, compound

HRID 1810897Notes

Reaction equation

HRID 1810897 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:16][C:17](=[O:36])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)[CH:19]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:15])=[O:5])[CH3:2].[BH4-].[Na+].CO>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([NH:16][C:17](=[O:36])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)[CH:19]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]1[OH:15])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 67076770HCID 67076770, compound

Product 1

HCID 67076718HCID 67076718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

The compound of step 1 (0.439 g, 0.900 mmol) was dissolved in THF (4 ml). The mixture was cooled to −30° C. and sodium borohydride (35 mg, 0.90 mmol) was added followed by dropwise addition of methanol. After 30 min, the mixture was partitioned between diethyl ether and 2 N hydrochloric acid, the aqueous phase was extracted with diethyl ether, the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to yield the title compound as a mixture of stereoisomers.

Workup

  1. customthe mixture was partitioned between diethyl ether and 2 N hydrochloric acid
  2. extractionthe aqueous phase was extracted with diethyl ether
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-3d551d40c32a4060a9abe6a1a25f4b1a
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

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