Water → HCID 88783904, compound

HRID 2398149Notes

Reaction equation

HRID 2398149 reaction equation
Br[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][CH:28]=[O:29])[C:25](=[O:30])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[CH3:31][C:32]([SH:34])=[O:33].C(N(CC)CC)C.O>CN(C)C=O.C(OCC)(=O)C>[C:32]([S:34][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][CH:28]=[O:29])[C:25](=[O:30])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])(=[O:33])[CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10484Thioacetic acidHCID 56977568HCID 56977568, compound

Product 1

HCID 88783904HCID 88783904, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of diphenylmethyl 3-bromomethyl-7β-formamidoceph-3-em-4-carboxylate, 1β-oxide (5.0 g) in N,N-dimethylformamide (30 ml) was treated with ethanethiolic acid (4.0 ml) and triethylamine (1.4 ml) and the reaction stirred for 1.6 hr. at +19°. The yellow solution was poured into water (100 ml) and ethyl acetate (100 ml) and the resulting insoluble solid was collected, washed with ethyl acetate and dried in vacuo over phosphorus pentoxide, to give diphenylmethyl 3-acetylthiomethyl-7β-formamidoceph-3-em-4-carboxylate, 1β-oxide (2.422 g, 49%), mp 198-199° (dec.), [α]D - 60° (c 1.0, DMSO), λmax. (EtOH) 273 nm (ε 10,300), νmax. (CHBr3) 3430 (NH), 1803 (β-lactam) 1725 (CO2R), 1695, 1505 (CONH), 1042 cm.-1 (S→O) τ (DMSO-d6), 1.66 (d J 9; NH), 1.78 (s; CHO), 2.59 (m, phenyl), 3.01 (s, CHPh2), 7.68 (s; SCH3).

Workup

  1. customat +19°
  2. customthe resulting insoluble solid was collected
  3. washwashed with ethyl acetate
  4. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-5f3886a938ad4b16a19482077af9a3cf
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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