Triethylamine → HCID 53635317, compound

HRID 1385822Notes

Reaction equation

HRID 1385822 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][CH:4]=[CH2:5].C(OC(Cl)=O)C.C(N(CC)CC)C.Cl.[CH2:22]([O:29][NH2:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[CH2:22]([O:29][NH:30][C:1](=[O:7])[CH2:2][CH2:3][CH:4]=[CH2:5])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 611384-Pentenoic acidHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 53635317HCID 53635317, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

This compound was prepared in several steps. 4-pentenoic acid (1.2.6.4) was reacted with ethylchloroformate in the usual way to obtain the active mixed anhydride. To a solution of the mixed anhydride in chloroform was added triethylamine and O-benzylhydroxylamine hydrochloride to obtain O-benzyl-4-pentenohydroxamic acid (1.2.6.5). The double bond was oxidized using osmium tetroxide/N-methylmorpholine oxide to give the diol (1.2.6.6). The terminal hydroxyl group was then protected with t-butyldimethylsilylchloride in the usual way to yield (1.2.6.7). The secondary hydroxyl group was tosylated using pyridine/p-toluenesulfonyl chloride. Cyclization of (1.2.6.8) to the corresponding pyrrolidone (1.2.6.9) was effected by using sodium carbonate in methanol. The protecting silyl group was removed by treatment with tetraethylammonium fluoride. The title compound (1.2.6.3) was prepared by reacting the latter compound (1.2.6.10) with pyridinelp-toluenesulfonyl chloride in the usual way.

Workup

  1. customThis compound was prepared in several steps
  2. customto obtain the

Sources & evidence

ORD record
ord-86f6bfbe3ab344d593c8e387f68657a7
Source dataset
uspto-grants-2001_07
Patent number
US06264966B1

Reaction notes

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