Water → HCID 86734343, compound

HRID 1974318Notes

Reaction equation

HRID 1974318 reaction equation
[CH2:1]([N:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:9][C:10]([C:12]1[CH:13]=[CH:14][C:15](OCCO)=[C:16]([CH:20]=1)[C:17]([NH2:19])=[O:18])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(=O)(O)[O-:34].[Na+].[C:38]([O:41][C:42](=O)[CH3:43])(=[O:40])[CH3:39]>C(O)(=O)C>[CH2:1]([N:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:9][C:10]([C:12]1[C:20]([O:34][CH2:43][CH2:42][O:41][C:38](=[O:40])[CH3:39])=[C:16]([CH:15]=[CH:14][CH:13]=1)[C:17]([NH2:19])=[O:18])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 21488958HCID 21488958, compound

Product 1

HCID 86734343HCID 86734343, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-(N,N-dibenzylglycyl)-2-(2-hydroxyethoxy)-benzamide (see Example 6(a)) (2.5 g) in acetic anhydride (10 ml) and acetic acid (10 ml) was heated at 100° for 1.25 hours, cooled, and poured into water. After being allowed to stand for 2 days at room temperature the aqueous solution was basified with sodium bicarbonate and extracted with ethyl acetate (3 × 100 ml). The dried extract was evaporated and the ether-soluble portion of the residue treated with ethereal hydrogen chloride. The precipitate (1.6 g) in water (50 ml) was basified with sodium bicarbonate solution and was extracted with ether (3 × 50 ml). The dried extracts were evaporated to give a solid m.p. 120°-128° (from ethyl acetate).

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate (3 × 100 ml)
  3. extractionThe dried extract
  4. customwas evaporated
  5. additionthe ether-soluble portion of the residue treated with ethereal hydrogen chloride
  6. extractionwas extracted with ether (3 × 50 ml)
  7. customThe dried extracts were evaporated

Sources & evidence

ORD record
ord-9947c028e4a747b5b7fe2c547b06d4d4
Source dataset
uspto-grants-1976_12
Patent number
US04000193

Reaction notes

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