Water → HCID 87421969, compound

HRID 510329Notes

Reaction equation

HRID 510329 reaction equation
[NH2:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6](/[CH:14]=[C:15]1/[C:16](=[O:36])[N:17]([C@@H:20]3[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]4[O:30][C:31](=[O:35])[O:32][C:33]=4[CH3:34])=[O:26])[CH2:21]3)[CH2:18][CH2:19]/1)=[C:7]2[C:11]([OH:13])=[O:12].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.Cl.[C:50]([O:69][N:70]=[C:71]([C:75]1[N:79]=[C:78]([NH2:80])[S:77][N:76]=1)[C:72](Cl)=[O:73])([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.O>ClCCl.CO>[NH2:80][C:78]1[S:77][N:76]=[C:75](/[C:71](=[N:70]/[O:69][C:50]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)/[C:72]([NH:1][C@@H:2]2[C:9](=[O:10])[N:8]3[C@@H:3]2[S:4][CH2:5][C:6](/[CH:14]=[C:15]2/[C:16](=[O:36])[N:17]([C@@H:20]4[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]5[O:30][C:31](=[O:35])[O:32][C:33]=5[CH3:34])=[O:26])[CH2:21]4)[CH2:18][CH2:19]/2)=[C:7]3[C:11]([OH:13])=[O:12])=[O:73])[N:79]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11708267BistrimethylsilylacetamidHCID 49818931HCID 49818931, compoundHCID 87420773HCID 87420773, compound

Product 1

HCID 87421969HCID 87421969, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

0.5 g of (6R, 7R)-7-amino-3[E-(R)-1′-(5-methyl-2-oxo-[1,3]-dioxol-4-ylmethoxycarbonyl)-2-oxo-[1,3′]bipyrrolidinyl-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid were dissolved in 20 ml of dichloromethane at 0°. 0.7ml of bis(trimethylsilyl)acetamide were then added and 0.46 g of 2-trityloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetic acid chloride hydrochloride (J. Antibiotics 37:557-571, 1984) were metered in portions. The mixture was poured onto 15 ml of water/15 ml of MeOH and the phases were separated. The water phase was washed once again with 15 ml of dichloromethane and the combined organic phases were dried over sodium sulfate and concentrated in vacuo.

Workup

  1. customthe phases were separated
  2. washThe water phase was washed once again with 15 ml of dichloromethane
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f5ea41c5554470181f238d1b33f9255
Source dataset
uspto-grants-2015_08
Patent number
US09096610B2

Reaction notes

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