Methanol → HCID 59506268, compound

HRID 1098769Notes

Reaction equation

HRID 1098769 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([C:22](=O)[CH3:23])[CH:10]=[CH:11][C:12]=2[S:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:4][CH:3]=1.CO.C([BH3-])#[N:28].[Na+].FC(F)(F)C(O)=O>>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([CH:22]([NH2:28])[CH3:23])[CH:10]=[CH:11][C:12]=2[S:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 59506297HCID 59506297, compound

Product 1

HCID 59506268HCID 59506268, compoundYield 43.5%

Procedure

To a solution of the compound yielded from step 3 (2.2 g, 5.7 mmol) in MeOH (30 mL) ammonium acetate (4.39 g, 57.0 mmol) and sodium cyanoborohydride (358 mg, 5.7 mmol) were added. The reaction mixture was refluxed for 4 h. After that the mixture was acidified with trifluoroacetic acid to pH=2 and then evaporated to dryness. Purification of the crude product by prep-HPLC and lyophilization of the relevant fractions gave the desired product (0.96g, 34%).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. customevaporated to dryness
  3. customPurification of the crude product by prep-HPLC and lyophilization of the relevant fractions

Sources & evidence

ORD record
ord-dd9bb812f12146fd9296e29798bd6447
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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