Anisole → HCID 13476964, compound

HRID 2164593Notes

Reaction equation

HRID 2164593 reaction equation
C1(C([O:14][C:15]([C:17]2[CH:18]3[CH:21]([CH2:22][C:23]=2[S:24][CH2:25][CH2:26][NH:27][C:28](=[O:30])[CH3:29])[CH:20]([CH:31]([OH:33])[CH3:32])[C:19]3=[O:34])=[O:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[C:28]([NH:27][CH2:26][CH2:25][S:24][C:23]1[CH2:22][CH:21]2[CH:18]([C:19](=[O:34])[CH:20]2[CH:31]([OH:33])[CH3:32])[C:17]=1[C:15]([OH:16])=[O:14])(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 53938917HCID 53938917, compound

Product 1

HCID 13476964HCID 13476964, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 50 mg of 3-(2-acetamidoethylthio)-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid diphenylmethyl ester and 25 μL of anisole in 1.5 mL of trifluoroacetic acid was stirred at room temperature for 10 min. The reaction mixture was evaporated to dryness, and trituration of the residue with ether afforded 30 mg (95%) of 3-(2-acetamidoethylthio)-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid as colorless, hydroscopic crystals. IR (Nujol mull) 1550, 1660, 1775 cm-1 ; NMR (400 MHz; acetone-d6): δ 1.24 (3H, d, J=6.5), 1.94 (3H, s), 2.98 (1H, m), 3.03 (2H, t, J=7), 3.14 (1H, ddd, J=18, 3.4, 1.2), 3.22 (1H, ddd, J=5.6, 3.9, 3.2), 3.35 (1H, dd, J=8.5, 1.7), 3.40 (2H, t, J=7), 4.05 (1H, qd, J=6.3, 4.9), 4.31 (1H, m), and 7.67 (1H, m).

Workup

  1. customThe reaction mixture was evaporated to dryness, and trituration of the residue with ether

Sources & evidence

ORD record
ord-c91a017f38c24b6080eb66a56d1b9f89
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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