Anisole → HCID 13476963, compound

HRID 2164585Notes

Reaction equation

HRID 2164585 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][CH:13]2[CH:10]([C:11](=[O:15])[CH2:12]2)[C:9]=1[C:16]([O:18]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][CH:13]2[CH:10]([C:11](=[O:15])[CH2:12]2)[C:9]=1[C:16]([OH:18])=[O:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 13476961HCID 13476961, compound

Product 1

HCID 13476963HCID 13476963, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 150 mg of 3-(2'-acetamidoethylthio)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester, and 130 mg of anisole in 1 mL of trifluoroacetic acid was stirred at ambient temperature for 15 min. The solvent was then removed by a stream of nitrogen leaving a residue which was crystallized from ether to afford 85 mg (92%) of 3-(2'-acetamidoethylthio)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid as colorless crystals, mp 150° to 152°. IR (Nujol): 1640, 1660, 1785, 3150 cm-1 ; NMR (CDCl3 /DMSO-d6): δ 1.93 (3H, s), 2.8-3.0 (5H, m), 3.1-3.4 (4H, m), 4.43 (1H, m), and 7.43 (1H, m). HRMS: The molecular ion (m/z 269) was not observed; however, a major fragment corresponding to loss of ketene from the molecular ion was mass measured: Calcd for C10H13O3NS, 227.0615; found, 227.0616.

Workup

  1. customThe solvent was then removed by a stream of nitrogen leaving a residue which
  2. customwas crystallized from ether

Sources & evidence

ORD record
ord-b14b6821c795420cab2ad4fad9aac2f9
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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