Acetic Anhydride → HCID 15280843, compound

HRID 1734653Notes

Reaction equation

HRID 1734653 reaction equation
[Cl:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([NH:6][C@H:7]2[C@@H:11]([OH:12])[C@@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[CH2:8]2)=[C:4]([N+:19]([O-:21])=[O:20])[CH:3]=1.C(O[C:26](=[O:28])[CH3:27])(=O)C>N1C=CC=CC=1>[C:11]([O:12][C@@H:11]1[C@H:7]([NH:6][C:5]2[CH:16]=[C:17]([Cl:18])[C:2]([Cl:1])=[CH:3][C:4]=2[N+:19]([O-:21])=[O:20])[CH2:8][C@H:9]([CH2:14][O:15][C:14](=[O:15])[CH3:9])[C@@H:10]1[O:13][C:26](=[O:28])[CH3:27])(=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15280840HCID 15280840, compound

Product 1

HCID 15280843HCID 15280843, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(1R, 2S, 3R, 5R)-5-(4,5-Dichloro-2-nitroanilino)-3-(hydroxymethyl)-1,2-cyclopentanediol (1.30 g, 3.86 mmol) was stirred in pyridine (10 mL)-acetic anhydride (2.2 mL) at ambient temperature for 2 days. Volatiles were evaporated in vacuo and the residue partitioned between chloroform and saturated aqueous sodium bicarbonate. The chloroform layer was dried (sodium sulfate) and concentrated to an oil which was chromatographed on silica gel. Elution with 2% methanol-chloroform gave (1R, 2S, 3R, 5R)-3-(acetoxymethyl)-5-(4,5-dichloro-2-nitroanilino)-1,2-cyclopentanediyl diacetate as yellow needles (1.60 g, 89%), after crystallization from ethyl acetate-hexanes, m.p. 125°-130° C.; 1H-NMR(DMSO-d6) and mass spectrum (CI) consistent with structure; [α]20589 -130.5°, [α]20578 -140°, [α]20546 -178° (c=0.275, methanol).

Workup

  1. customVolatiles were evaporated in vacuo
  2. customthe residue partitioned between chloroform and saturated aqueous sodium bicarbonate
  3. dry with materialThe chloroform layer was dried (sodium sulfate)
  4. concentrationconcentrated to an oil which
  5. customwas chromatographed on silica gel
  6. washElution with 2% methanol-chloroform

Sources & evidence

ORD record
ord-e1c8bfa2aa3944759acecf9eb498bde6
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

Loading…