Ethyl Acetate → HCID 57219839, compound

HRID 2164586Notes

Reaction equation

HRID 2164586 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]([OH:18])=[O:17])(=[O:3])[CH3:2].C(OC(=O)C)C.[C:25]1([CH:35]=[N+]=[N-])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>CO>[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][CH2:35][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12576845Naphthalene, 1-(diazomethyl)-HCID 13476963HCID 13476963, compound

Product 1

HCID 57219839HCID 57219839, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 100 mg of 3-(2'-acetamidoethylthio)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid in 5 mL of a mixture of ethylacetate and methanol was treated with a slight excess of α-naphthyldiazomethane. After the solution was stirred for 1 hr and then concentrated on a rotary evaporator, the crude product was purified by preparative thin layer chromatography on a 20×20×0.2 cm silica gel plate eluted with 5% methanol in methylene chloride affording 130 mg (85.5%) of 3-(2'-acetamidoethylthio)7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, 1-naphthylmethyl ester, as a glass. IR (neat): 3200, 1780, 1690, 1660 cm-1 ; NMR (220 MHz; CDCl3): δ 1.86 (3H, s), 2.6-3.0 (5H, m), 3.0-3.5 (4H, m), 4.43 (1H, m), 5.61 (1H, d, J=18), 5.64 (1H, d, J=18 ), 6.30 (1H, m), and 7.3-8.2 (7H, m); MS (chemical ionization) confirmed molecular weight of 409.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customthe crude product was purified by preparative thin layer chromatography on a 20×20×0.2 cm silica gel plate
  3. washeluted with 5% methanol in methylene chloride affording 130 mg (85.5%) of 3-(2'-acetamidoethylthio)7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, 1-naphthylmethyl ester, as a glass

Sources & evidence

ORD record
ord-e72a88ad61a6443bab107523b2365970
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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