Acetic Acid → HCID 10314068, compound

HRID 1453780Notes

Reaction equation

HRID 1453780 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)[O:3][CH2:2]1.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([NH:22][CH2:21][C:20]3[CH:23]=[CH:24][C:17]([F:16])=[CH:18][CH:19]=3)[CH2:11][CH2:10]2)[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 673264-FluorobenzylamineHCID 5003444Sodium cyanoborohydrideHCID 57430094HCID 57430094, compound

Product 1

HCID 10314068HCID 10314068, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 128NLS50 (1.73 g, 8.13 mmol) in methanol (100 mL) was added dropwise 4-fluorobenzylamine (0.93 mL, 8.13 mmol) and acetic acid. Sodium cyanoborohydride (2.15 g, 40 mmol) was added slowly to the mixture at 0° C. and stirring was continued at rt overnight. The reaction mixture was concentrated in vacuo and the residue partitioned between dichloromethane and 1M NaOH, the aqueous layer extracted twice with dichloromethane and the combined organic layers dried over Na2SO4, filtered and evaporated to dryness. Purification of the residue by a short silica gel column chromatography eluting with 0-30% methanol in dichloromethane gave the title compound (1.51 g, 58%) as a colourless solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between dichloromethane and 1M NaOH
  3. extractionthe aqueous layer extracted twice with dichloromethane
  4. dry with materialthe combined organic layers dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification of the residue by a short silica gel column chromatography
  8. washeluting with 0-30% methanol in dichloromethane

Sources & evidence

ORD record
ord-1df7900cf2f54ed1bac7244275412397
Source dataset
uspto-grants-2009_01
Patent number
US07476682B2

Reaction notes

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