Benzenepropanal → HCID 58604475, compound

HRID 1743245Notes

Reaction equation

HRID 1743245 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH:9]1[C:16](=[O:17])[N:15]2[CH:11]([S:12][CH2:13][CH:14]2[C:18]#[N:19])[CH2:10]1.[C:20]1([CH2:26][CH2:27][CH:28]=O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(COC)OC.C(O)(=O)C>[O:17]=[C:16]1[N:15]2[C@@H:11]([S:12][CH2:13][C@H:14]2[C:18]#[N:19])[CH2:10][C@H:9]1[NH:8][CH2:28][CH2:27][CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 7707BenzenepropanalHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 22238407HCID 22238407, compound

Product 1

HCID 58604475HCID 58604475, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

30 mg of (3R,6R,7aS)-(6-amino-5-oxohexahydropyrrolo[2,1-b]thiazole-3-carbonitrile trifluoroacetate, 0.0132 ml of 3-phenylpropionaldehyde and 0.115 ml of glacial acetic acid were heated in 1.5 ml of methylene chloride at 40° C. for 20 minutes. The mixture was then cooled to room temperature, 8.3 mg of sodium acetate, 0.5 ml of dimethoxyethane and 27.8 mg of sodium triacetoxyborohydride were added, and the mixture was stirred at RT overnight. After concentration of the mixture, the residue was purified by column chromatography (silica gel, mobile phase: ethyl acetate: n-heptane=8:1).

Workup

  1. customAfter concentration of the mixture, the residue was purified by column chromatography (silica gel, mobile phase: ethyl acetate: n-heptane=8:1)

Sources & evidence

ORD record
ord-f99a26c415854f909768ae54381a8488
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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