Chloroacetic Acid → HCID 178441402, compound

HRID 1493677Notes

Reaction equation

HRID 1493677 reaction equation
C(=O)([O-])[O-].[Ba+2].[Cl:6][CH2:7][C:8]([OH:10])=[O:9].[CH3:11][CH2:12][CH2:13][CH2:14][CH:15]1[C:50](=[O:51])[O:49][CH:48]([CH:52]([CH:54]([OH:62])[CH2:55][CH2:56][CH2:57][NH:58][C:59]([NH2:61])=[NH:60])[CH3:53])[CH:47]([CH3:63])[CH:46]=[C:45]([CH3:64])[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]([OH:65])[CH2:39][CH:38]([OH:66])[CH2:37][CH:36]([OH:67])[CH2:35][CH:34]([OH:68])[CH2:33][CH:32]([OH:69])[CH:31]([O:70][C@H:71]2[O:75][C@H:74]([CH2:76][OH:77])[C@@H:73]([OH:78])[C@@H:72]2[OH:79])[CH:30]=[C:29]([CH3:80])[CH:28]([OH:81])[CH2:27][CH2:26][CH2:25][CH:24]([OH:82])[CH2:23][CH2:22][CH2:21][CH:20]([OH:83])[CH2:19][CH2:18][CH:17]([CH3:84])[CH:16]1[OH:85].S([O-])([O-])(=O)=O>CO.O>[CH3:11][CH2:12][CH2:13][CH2:14][CH:15]1[C:50](=[O:51])[O:49][CH:48]([CH:52]([CH:54]([OH:62])[CH2:55][CH2:56][CH2:57][NH:58][C:59]([NH2:61])=[NH:60])[CH3:53])[CH:47]([CH3:63])[CH:46]=[C:45]([CH3:64])[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]([OH:65])[CH2:39][CH:38]([OH:66])[CH2:37][CH:36]([OH:67])[CH2:35][CH:34]([OH:68])[CH2:33][CH:32]([OH:69])[CH:31]([O:70][C@H:71]2[O:75][C@H:74]([CH2:76][OH:77])[C@@H:73]([OH:78])[C@@H:72]2[OH:79])[CH:30]=[C:29]([CH3:80])[CH:28]([OH:81])[CH2:27][CH2:26][CH2:25][CH:24]([OH:82])[CH2:23][CH2:22][CH2:21][CH:20]([OH:83])[CH2:19][CH2:18][CH:17]([CH3:84])[CH:16]1[OH:85].[Cl:6][CH2:7][C:8]([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 300Chloroacetic AcidHCID 10563Barium CarbonateHCID 178441404HCID 178441404, compound

Product 1

HCID 178441402HCID 178441402, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

0.088 g (0.446 millimoles) of barium carbonate and 0.21 g (2.23 millimoles) of monochloro acetic acid are dissolved in 10 ml of a 1:1 mixture of methanol and water under heating. The still hot solution is added to a suspension of 1.0 g (0.887 millimoles) of primycin sulfate and 70 ml of methanol. The reaction mixture is heated to boiling for 10 minutes under constant stirring, the precipitated barium sulfate is filtered through Celite. The filtrate is evaporated in vacuo. The solid residue is treated with ether. The white powdery solid is washed on the filter three times with 10 ml of ether saturated with water each and dried to constant weight. Thus 0.97 g of primycin monochloroacetate is obtained, yield 93.3%. Mp.: 176° C., /α/D25 =+22.0°.

Workup

  1. temperatureunder heating
  2. temperatureThe reaction mixture is heated
  3. filtrationthe precipitated barium sulfate is filtered through Celite
  4. customThe filtrate is evaporated in vacuo
  5. additionThe solid residue is treated with ether
  6. washThe white powdery solid is washed on the
  7. filtrationfilter three times with 10 ml of ether saturated with water each and
  8. customdried to constant weight

Sources & evidence

ORD record
ord-5e1484bba8c74f35aa16d710d3115ec4
Source dataset
uspto-grants-1991_06
Patent number
US05023242

Reaction notes

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