Methanol → HCID 172930683, compound

HRID 247763Notes

Reaction equation

HRID 247763 reaction equation
[I-].[C:2]([NH:21][C:22]1[S:23][CH:24]=[C:25](/[C:27](=[N:76]/[O:77][CH3:78])/[C:28]([NH:30][CH:31]2[C:74](=[O:75])[N:33]3[C:34]([C:58]([O:60][CH:61]([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)=[O:59])=[C:35]([CH2:38][P+:39]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:36][S:37][C@H:32]23)=[O:29])[N:26]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].C(Cl)(Cl)Cl.CO>ClCCl>[C:2]([NH:21][C:22]1[S:23][CH:24]=[C:25](/[C:27](=[N:76]/[O:77][CH3:78])/[C:28]([NH:30][CH:31]2[C:74](=[O:75])[N:33]3[C:34]([C:58]([O:60][CH:61]([C:68]4[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=4)[C:62]4[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=4)=[O:59])=[C:35]([CH:38]=[P:39]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[CH2:36][S:37][C@H:32]23)=[O:29])[N:26]=1)([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 172932298HCID 172932298, compound

Product 1

HCID 172930683HCID 172930683, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(triphenylphosphonio)methyl]-3-cephem-4-carboxylate iodide* (3.0 g, 2.5 m moles) in dichloromethane (40 ml) was shaken with 1N NaOH (10 ml) until the spot of the starting material disappeared on TLC (silica gel, CHCl3 --MeOH=10:1). Organic layer was separated and concentrated under reduced pressure. The residue was triturated with n-hexane and the product was collected by filtration to give 2.5 g (93%) of the title compound.

Workup

  1. customOrganic layer was separated
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with n-hexane
  4. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-78b3c045a7794887a9cc043cff610b4d
Source dataset
uspto-grants-1987_11
Patent number
US04708955

Reaction notes

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