Triphenylphosphine → HCID 88802229, compound

HRID 2419861Notes

Reaction equation

HRID 2419861 reaction equation
[Br:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[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].[C:37]1([P:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1C=CC=CC=1.CCOCC>[Br-:1].[C:13]1([CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:11][C:9]([C:8]2[N:7]3[C:25](=[O:36])[C@@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)[C@H:6]3[S:5][CH2:4][C:3]=2[CH2:2][P+:43]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:10])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 70592080HCID 70592080, compound

Product 1

HCID 88802229HCID 88802229, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of diphenylmethyl 3-bromomethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (300 mg.), Rf 0.6 in benzene (5 ml.) was treated with triphenylphosphine (140 mg.) and the total warmed to 50° for 10 minutes. After the mixture had stood at room temperature for a further hour it was diluted with ether and the precipitated solid was collected by filtration. This material was washed thoroughly with ethyl acetate and ether, and on drying in vacuo gave the phosphonium bromide (250 mg.) Rf 0.0 m.p. 135° - 140° C (decomp.) [α]D + 12° (tetrahydrofuran), νmax (CHBr3) 3410 (NH), 1784 (β-lactam), 1710 (CO2R), 1680 and 1515 (CONH) and 1442 (P--C aryl.) cm.-1 τ (CDCl3) 4.38 (C(7) --H, dd, J 4.5 and 9 Hz), 5.19 (C(6) --H, d, J 4.5 Hz), 4.62 and 4.8 (CH2 -- P, two d, JP-H 16 Hz), 6.02 and 6.6 (C(2) -- CH2, two dd, JH-H 18 Hz and JP-H 3-4 Hz).

Workup

  1. temperaturethe total warmed to 50° for 10 minutes
  2. waitAfter the mixture had stood at room temperature for a further hour
  3. filtrationthe precipitated solid was collected by filtration
  4. washThis material was washed thoroughly with ethyl acetate and ether
  5. customon drying in vacuo

Sources & evidence

ORD record
ord-8d54f7ef39db4904889aa56c851bf17c
Source dataset
uspto-grants-1978_08
Patent number
US04107431

Reaction notes

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