Ethanol → HCID 178469035, compound

HRID 1762489Notes

Reaction equation

HRID 1762489 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N:23]=[CH:24][NH:25][C:26]3[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=3)[CH:21]=2)[NH:16][CH:15]=1.C([O:39][CH2:40][CH3:41])C.[CH2:42]([OH:44])[CH3:43]>CN.C(=O)(O)[O-].[Na+]>[C:40]([OH:39])(=[O:44])/[CH:41]=[CH:29]\[C:30]([OH:32])=[O:31].[C:30]([OH:32])(=[O:31])/[CH:29]=[CH:43]\[C:42]([OH:39])=[O:44].[CH2:33]([O:32][C:30](=[O:31])[C:29]1[CH:28]=[CH:27][C:26]([NH:25][CH:24]=[N:23][C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[CH2:13][CH2:12][NH2:3])=[CH:36][CH:35]=1)[CH3:34]

Participants

6

Reactant 3

HCID 702Ethanol2×HCID 3283Diethyl EtherHCID 178469034HCID 178469034, compound

Product 1

HCID 178469035HCID 178469035, compound

Reagents, catalysts & solvents 2

HCID 6329MethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of the product of Stage (i) in absolute ethanol (16 ml) and methylamine in ethanol (33% w/w 8 ml) was stirred at room temperature for 1.5 h. The solution was diluted with 8% sodium bicarbonate solution (ca 50 ml) and the mixture extracted with ethyl acetate (3×20 ml). The extracts were dried (Na2SO4), reduced to dryness under vacuo and the residue chromatographed on silica (A). The required fractions were collected and reduced to dryness. The residue (71 mg) was dissolved in a minimum quantity of absolute ethanol and a solution of maleic acid (47 mg) in ethanol (2 ml) added. The mixture was reduced to dryness and the foam obtained stirred with dry diethyl ether (ca 5 ml). The resulting solid was collected and dried to give the title compound as a powder (78 mg), m.p. 100°-105°.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×20 ml)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. customthe residue chromatographed on silica (A)
  4. customThe required fractions were collected
  5. dissolutionThe residue (71 mg) was dissolved in a minimum quantity of absolute ethanol
  6. additiona solution of maleic acid (47 mg) in ethanol (2 ml) added
  7. customthe foam obtained
  8. customThe resulting solid was collected
  9. customdried

Sources & evidence

ORD record
ord-331fceae21fc486b97f563f27d9b4bdc
Source dataset
uspto-grants-1989_05
Patent number
US04833153

Reaction notes

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