4-Methoxyphenylacetic Acid → HCID 131716750, compound

HRID 703406Notes

Reaction equation

HRID 703406 reaction equation
[CH2:1]([C@H:3]1[C@@H:6]([CH2:7][OH:8])[N:5]([S:9]([C:12]2[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])[C:4]1=[O:19])[CH3:2].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=[O:30])=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([C@H:3]1[C@@H:6]([CH2:7][O:8][C:29](=[O:30])[CH2:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[N:5]([S:9]([C:12]2[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])[C:4]1=[O:19])[CH3:2]

Participants

6

Reactant 3

HCID 76904-Methoxyphenylacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 67940826HCID 67940826, compound

Product 1

HCID 131716750HCID 131716750, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To (±)-cis-3-ethyl-4-hydroxymethyl-N-toluenesulfonyl-2-azetidinone (3.3 mg) and p-methoxyphenylacetic acid (3.7 mg) in CH2Cl2 (0.6 ml) was added dicyclohexylcarbodiimide (DCC) (5 mg) followed by p-dimethylaminopyridine (DMAP) (1 mg). The mixture was stirred overnight, at room temperature and then purified via preparative tlc on a silica gel plate and developed with CH2Cl2 to yield the titled compound.

Workup

  1. custompurified via preparative tlc on a silica gel plate

Sources & evidence

ORD record
ord-83e557014090403ca8dc43edc701801f
Source dataset
uspto-grants-1991_01
Patent number
US04983597

Reaction notes

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