Triphenylphosphine → HCID 18607841, compound

HRID 2419871Notes

Reaction equation

HRID 2419871 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]1[CH2:23][S:24][C@@H:25]2[C@H:45]([NH:46][CH:47]=[O:48])[C:44](=[O:49])[N:26]2[C:27]=1[C:28]([O:30][CH:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>C(OCC)(=O)C>[Br-:20].[C:38]1([CH:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:30][C:28]([C:27]2[N:26]3[C:44](=[O:49])[C@@H:45]([NH:46][CH:47]=[O:48])[C@H:25]3[S:24][CH2:23][C:22]=2[CH2:21][P+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:29])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 56977568HCID 56977568, compound

Product 1

HCID 18607841HCID 18607841, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of triphenylphosphine (1.47 g, 1.5 equiv.) in ethyl acetate (10 ml) was added to a stirred solution of diphenylmethyl 3-bromomethyl-7β-formamidoceph-3-em-4-carboxylate (1.82 g, 3.725 mmole) in ethyl acetate (50 ml). The mixture was stirred overnight at ca. 20° out of direct light, and the precipitated solid was filtered off, washed with ethyl acetate and dried to give the title phosphonium salt (2.41 g, 86%), λmax. (EtOH) 268.5 nm (ε 8,700) and 275.5 nm (ε 8,150), νmax. (CHBr3) 3440 (NH), (1788 azetidin-2-one), 1710 (CO2R), 1680 and 1500 (CONH) and 1443 cm-1 (P+ --C6H5), τ (CDCl3) 1.45 (1H,d, J 9 Hz; NH), 1.73 (1H, s; CHO), 3.57 (1H, s; (C6H5)2CH), 4.32 (1H,dd, J 9 and 5 Hz; C7 --H), 4.62 and 4.78 (2H, centres of 2 AB-quartets, JP-H 16 Hz, JH-H 15 Hz; C3 --CH2P+), 5.12 (1H,d, J 5 Hz; C6 -H), 6.06 and 6.60 (2H, broadened AB-q, J 18 Hz; C2 -H2).

Workup

  1. filtrationthe precipitated solid was filtered off
  2. washwashed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-930b62ebbf6d4128a027b6da8ceb87fe
Source dataset
uspto-grants-1978_08
Patent number
US04107431

Reaction notes

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