Triphenylphosphine → HCID 178451387, compound

HRID 979385Notes

Reaction equation

HRID 979385 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][C:47](=[O:84])/[C:48](=[N:74]\[O:75][CH2:76][C:77]([O:79][C:80]([CH3:83])([CH3:82])[CH3:81])=[O:78])/[C:49]3[N:50]=[C:51]([NH:54][C:55]([C:68]4[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=4)([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)[C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[S:52][CH:53]=3)[C:44](=[O:85])[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:80]([O:79][C:77]([CH2:76][O:75]/[N:74]=[C:48](/[C:49]1[N:50]=[C:51]([NH:54][C:55]([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)([C:68]2[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=2)[C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[S:52][CH:53]=1)\[C:47]([NH:46][C@@H:45]1[C:44](=[O:85])[N:26]2[C:27]([C:28]([O:30][CH:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:29])=[C:22]([CH2:21][P+:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:23][S:24][C@H:25]12)=[O:84])=[O:78])([CH3:81])([CH3:82])[CH3:83]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 172953016benzhydryl (6R,7R)-3-(bromomethyl)-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 178451387HCID 178451387, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of triphenylphosphine (0.524 g) and diphenylmethyl (6R,7R)-3-bromomethyl-7-[(Z)-2-(t-butoxycarbonylmethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]ceph-3-em-4-carboxylate (0.985 g) [prepared according to the method of UK Patent Specification No. 2036738A] in ethyl acetate (10 ml) was stirred at ambient temperature for 16 hr. During this time, a solid was deposited. This was filtered off, washed with ethyl acetate, and dried in vacuo to give the title compound (0.848 g); νmax (CHBr3) 3385, 3280 (NH), 1790 (β-lactam), 1728, 1720 (ester), 1680, 1522 cm-1 (amide).

Workup

  1. filtrationThis was filtered off
  2. washwashed with ethyl acetate
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e47710765f51462da5049d93c923ae6b
Source dataset
uspto-grants-1987_05
Patent number
US04666899

Reaction notes

Loading…