Sodium cyanoborohydride → HCID 54303410, compound

HRID 1904400Notes

Reaction equation

HRID 1904400 reaction equation
[C:1]1([O:11][CH2:12][CH:13]([OH:23])[CH2:14][NH:15][CH:16]([CH3:22])[CH2:17][CH2:18][C:19](O)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:24]([NH:28][C:29](=[O:37])[CH2:30]CCCC(=O)C)[CH2:25][CH2:26][CH3:27].C([BH3-])#N.[Na+]>CO>[CH2:24]([NH:28][C:29](=[O:37])[CH2:30][CH2:19][CH2:18][CH2:17][CH:16]([NH:15][CH2:14][CH:13]([OH:23])[CH2:12][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:22])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 12857138HCID 12857138, compoundHCID 20038907HCID 20038907, compound

Product 1

HCID 54303410HCID 54303410, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized by the method given for Compound 7 using the following quantities: Compound V (R=1-naphthyl) (0.177 g, 0.5 mmol), 6-oxoheptanoic acid n-butylamide (0.100 g, 0.5 mmol), sodium cyanoborohydride (0.32 g, 0.5 mmol), methanol (2 ml). Purification of a portion of the product after extraction was achieved by semipreparative high pressure liquid chromatography using a C18 column, 1.3 ml/min flow rate with 64% methanol/0.01N hydrochloric acid as eluant. The appropriate fractions were combined, the solvent evaporated under reduced pressure and the residue lyophilized from methanol/water to give 13.8 mg of the hydrochloride salt of the desired compound. The purity of the product was verified by HPLC (1.2 ml/min, 64% methanol/0.01N hydrochloric acid, ret. time=20 min).

Workup

  1. customPurification of a portion of the product
  2. extractionafter extraction
  3. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-4c5aecdcb6284f87913444a1c5419a0e
Source dataset
uspto-grants-1989_06
Patent number
US04837305

Reaction notes

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