Diethyl Ether → HCID 390251, compound

HRID 1604920Notes

Reaction equation

HRID 1604920 reaction equation
[OH:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:22])[CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:12](=[O:23])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10].[C:24]1([C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N+]=[N-])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCOCC>O1CCCC1>[OH:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:22])[CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:12](=[O:23])[N:7]2[C:8]=1[C:9]([O:11][CH:30]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 930153-(Hydroxymethyl)-7-{[1-hydroxy-2-(thiophen-2-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 390251HCID 390251, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxymethyl-7β-(2'-thienylacetamido)ceph-3-em-4-carboxylic acid (500 mg.) was dissolved in dry tetrahydrofuran and treated with a solution of diphenyldiazomethane (300 mg., 1.1 equiv.) in petrol. Nitrogen was evolved slowly, and after 21/2 hours the solution was evaporated, the residue dissolved in ethyl acetate, and the solution was washed with bicarbonate solution and re-evaporated. This gave a gum which solidified on trituration with ether (0.5 g.). A sample was recrystallised from methanol, m.p. 164°, [α]D23 = + 25° (c, 1.0, dioxan), +22° (c 1.0, tetrahydrofuran). λλmax. ethanol 234 nm. E1 cm1% = 255, (ε = 13,300), 259 nm. E1cm1% = 151 (ε 7,850), νmax. (bromoform) 3420 (OH), 3280 (NH), 1750 (β-lactam), 1722 cm-1 (COOR). (Found, C, 62.2; H, 4.5; N, 5.4; S, 12.1. C27H24N2O5S2 requires C, 62.3; H, 4.7; N, 5.4; S, 12.3%) RF = 0.83 (Kieselgel G plates; ethyl acetate:benzene=1:2).

Workup

  1. customafter 21/2 hours the solution was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washthe solution was washed with bicarbonate solution
  4. customre-evaporated
  5. customThis gave a gum which
  6. customA sample was recrystallised from methanol, m.p. 164°, [α]D23 = + 25° (c, 1.0, dioxan), +22° (c 1.0, tetrahydrofuran)

Sources & evidence

ORD record
ord-a414811c46cd41b39cb19d2df967dd53
Source dataset
uspto-grants-1976_04
Patent number
US03948906

Reaction notes

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