2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → HCID 141572538, compound

HRID 1886690Notes

Reaction equation

HRID 1886690 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:71]/[O:72][CH3:73])/[C:27]([NH:29][CH:30]2[C:69](=[O:70])[N:32]3[C:33]([C:57]([O:59][CH2:60][C:61]4[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][CH:62]=4)=[O:58])=[C:34]([CH:37]=P(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:74]([O:81][CH2:82][CH:83]=O)([C:77]([CH3:80])([CH3:79])[CH3:78])([CH3:76])[CH3:75]>ClCCl.CCCCCC.C(OCC)(=O)C>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:71]/[O:72][CH3:73])/[C:27]([NH:29][CH:30]2[C:69](=[O:70])[N:32]3[C:33]([C:57]([O:59][CH2:60][C:61]4[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][CH:62]=4)=[O:58])=[C:34](/[CH:37]=[CH:83]\[CH2:82][O:81][Si:74]([C:77]([CH3:78])([CH3:79])[CH3:80])([CH3:75])[CH3:76])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 141572544HCID 141572544, compound

Product 1

HCID 141572538HCID 141572538, compoundYield 45.8%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-methoxyphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(triphenylphosphoranylidene)methyl- 3-cephem-4-carboxylate (10.5 g; 10.30 mmol) and t-butyldimethylsilyloxyacetaldehyde (2.58 g; 14.83 mmol) in dichloromethane (100 ml) was stirred at room temperature for 16 hours. After the solvent was distilled off under reduced pressure, the residue was purified by chromatography on a silica gel column (n-hexane:ethyl acetate=2.5:1) whereby the title compound (4.30 g; 4.72 mmol; 45.8%) was obtained.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a4f6c3e1cc0240999d1d4102be14f33c
Source dataset
uspto-grants-1992_09
Patent number
US05151417

Reaction notes

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