Methanol → HCID 59506145, compound

HRID 1098764Notes

Reaction equation

HRID 1098764 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:16](=O)[CH3:17])[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:9].CO.C([BH3-])#[N:22].[Na+]>>[NH2:22][CH:16]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[C:2]([Br:1])[CH:3]=1)[CH3:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 59506284HCID 59506284, compound

Product 1

HCID 59506145HCID 59506145, compound

Procedure

To a solution of the compound yielded from step 4 (160 mg, 0.51 mmol) in MeOH (3 mL) ammonium acetate (395 mg, 5.13 mmol) and sodium cyanoborohydride (32 mg, 0.513 mmol) were added. The reaction mixture was refluxed for 3 h. Then the mixture was quenched by addition of trifluoroacetic acid (pH=2) and evaporated to dryness. Purification of the crude product by prep-HPLC and lyophilization of the relevant fractions leads to the desired product.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customThen the mixture was quenched by addition of trifluoroacetic acid (pH=2)
  3. customevaporated to dryness
  4. customPurification of the crude product by prep-HPLC and lyophilization of the relevant fractions

Sources & evidence

ORD record
ord-4e816a4074cb45f49434223d61eea60e
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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