Dicyclohexylcarbodiimide → HCID 86736920, compound

HRID 2049229Notes

Reaction equation

HRID 2049229 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][C:4]=1[CH2:13][O:14][CH3:15].[NH2:16][C:17]1([O:32][CH3:33])[C:23](=[O:24])[N:22]2[CH:18]1[S:19][C:20]([CH3:31])([CH3:30])[CH:21]2[C:25]([O:27][CH2:28][CH3:29])=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:16][C:17]2([O:32][CH3:33])[C:23](=[O:24])[N:22]3[CH:18]2[S:19][C:20]([CH3:30])([CH3:31])[CH:21]3[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:12])=[CH:5][C:4]=1[CH2:13][O:14][CH3:15]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 5360545SodiumHCID 20344782HCID 20344782, compoundHCID 86736921HCID 86736921, compound

Product 1

HCID 86736920HCID 86736920, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Equivalent amouts (0.05 mole) of the sodium salt of 4-hydroxy-3-(methoxymethyl)benzeneacetic acid and 6-amino-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylic acid, ethyl ester, are added to dimethylformamide (DMF). The temperature is maintained at 0° C. Then about 1.2 equivalents of dicyclohexylcarbodiimide in DMF is added. The mixture is stirred at 0° C. for from 0.5 to 3 hours and an additional 2 to 5 hours at room temperature. Filtration of the reaction mixture removes the formed dicyclohexylurea. The filtrate is then diluted with chloroform, methylene chloride or ethyl acetate, washed with water, dried and evaporated to give the title compound.

Workup

  1. filtrationFiltration of the reaction mixture
  2. customremoves the formed dicyclohexylurea
  3. additionThe filtrate is then diluted with chloroform, methylene chloride or ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-160341866dd246de9141e906f55d678e
Source dataset
uspto-grants-1980_04
Patent number
US04197240

Reaction notes

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