Trichloroacetic Acid → HCID 131716586, compound

HRID 1032642Notes

Reaction equation

HRID 1032642 reaction equation
[CH2:1]([O:19][C:20]1[C:21]([O:23][C@H:24]([C@H:27]([CH2:29][OH:30])[OH:28])[C:25]=1[OH:26])=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:31]1([N:37]=[C:38]=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.ClC(Cl)(Cl)C(O)=O>C(Cl)(Cl)Cl>[C:31]1([NH:37][C:38]([O:30][CH2:29][C@H:27]([OH:28])[C@H:24]2[O:23][C:21](=[O:22])[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:25]2[OH:26])=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 7672Phenyl isocyanateHCID 54694681HCID 54694681, compound

Product 1

HCID 131716586HCID 131716586, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-O-octadecyl-L-ascorbic acid (0.8 g, 2 mmole) and phenylisocyanate (0.24 g, 2 mmole) in chloroform (20 ml) was added trichloracetic acid (0.1 ml). The mixture was heated at 60° C. for one hour, which was washed with water, dried and concentrated to give a product. The product was recrystallized from isopropyl ether - ethyl acetate to give 6-O-phenylcarbamoyl-2-O-octadecyl-L-ascorbic acid (0.75 g), m.p. 149°-150° C. C31H49NO7 (Found: C,68.14; H,9.08; N,2.74%. Anal. Calcd: C,67.98; H,9.02; N,2.56).

Workup

  1. washwhich was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customto give a product
  5. customThe product was recrystallized from isopropyl ether - ethyl acetate

Sources & evidence

ORD record
ord-6458cc0813dc45c2832d4e5000f6c823
Source dataset
uspto-grants-1990_09
Patent number
US04959362

Reaction notes

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