Benzaldehyde → HCID 86600964, compound

HRID 2074983Notes

Reaction equation

HRID 2074983 reaction equation
[NH:1]([C:3]([C@H:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:6][N:7]([OH:10])[CH:8]=[O:9])=[O:4])[NH2:2].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO>[CH2:16]([NH:2][NH:1][C:3]([C@H:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:6][N:7]([OH:10])[CH:8]=[O:9])=[O:4])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 6

HCID 240BenzaldehydeHCID 313Hydrochloric Acid2×HCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86600963HCID 86600963, compound

Product 1

HCID 86600964HCID 86600964, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

N-[(R)-2-(Hydrazinocarbonyl)-heptyl]-N-hydroxy-formamide (50 mg, 0.23 mmoles) and benzaldehyde (24 mg, 0.23 mmoles) were dissolved in methanol (2 mL) under argon in the. presence of 4 Å molecular sieves (50 mg), stirred for 1 hour and cooled to 0° C. To the mixture was added one crystal of methyl orange indicator and enough methanolic HCl to keep the solution acidic (red color). Sodium cyanoborohydride (17 mg, 0.28 mmoles) was added, along with enough methanolic HCl to keep the solution acidic (red indicator). The system was warmed to room temperature, stirred for two days, neutralized with sodium bicarbonate solution, and extracted with ethyl acetate (3×). The organic layer was dried over anhydrous sodium sulfate, concentrated to dryness and purified by prep hplc to afford the title compound. MH+308.

Workup

  1. temperatureThe system was warmed to room temperature
  2. stirringstirred for two days
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. custompurified by prep hplc

Sources & evidence

ORD record
ord-844680561a614c0c840e9049664f1efa
Source dataset
uspto-grants-2011_04
Patent number
US07919528B2

Reaction notes

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