Hydrochloric Acid → HCID 86746931, compound

HRID 1587475Notes

Reaction equation

HRID 1587475 reaction equation
[C@H:1]1([O:12][CH2:13][C:14]2[O:18][C:17]([CH:19]=[N:20]O)=[CH:16][CH:15]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[C:22]([O-:25])(=O)[CH3:23].[Na+].Cl.ClCCl>C(OC(=O)C)(=O)C.C1(C)C=CC=CC=1.CC(C)=O.C(Cl)(Cl)Cl>[C:2]([O:3][C@@H:2]1[C@@H:4]([O:5][C:4](=[O:5])[CH3:6])[C@H:6]([O:7][C:8](=[O:9])[CH3:10])[C@@H:8]([CH2:10][O:11][C:22](=[O:25])[CH3:23])[O:9][C@@H:1]1[O:12][CH2:13][C:14]1[O:18][C:17]([C:19]#[N:20])=[CH:16][CH:15]=1)(=[O:3])[CH3:1]

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6344DichloromethaneHCID 517045Sodium Acetate2×HCID 86746932HCID 86746932, compound3×

Product 1

HCID 86746931HCID 86746931, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 7918Acetic AnhydrideSolventHCID 20247278Toluene acetoneSolvent

Procedure

A suspension of 3.0 g (10 mmol) GMF oxime (formula 9, product of Example 9) and 1.0 g freshly-melted sodium acetate in 10 ml acetic anhydride was stirred for 30 min at room temperature. The now clear solution was then made slightly acid with mineral acid by addition of hydrochloric acid (4 ml 4N HCl, 1.3 mole equiv. based on the sodium acetate used) and heated for a short time (5-8 min) to 60° C. Stirring into ice water, extraction with dichloromethane and evaporation of the combined extracts gave 3.5 g (78%) of the nitrile of formula (14) as a chromatographically homogenous syrup with Rf =0.31 (TCL in toluene/acetone, 4:1) and [α]D20 =+135° (c=0.7, chloroform).

Workup

  1. temperatureheated for a short time (5-8 min) to 60° C

Sources & evidence

ORD record
ord-3ad6eb86039f403cb70e04cf04cfe4ad
Source dataset
uspto-grants-1993_06
Patent number
US05218098

Reaction notes

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