Acetic Anhydride → HCID 15280843, compound

HRID 1609045Notes

Reaction equation

HRID 1609045 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-5a6e656d24f24a0895259eaf22e3aeb2
Source dataset
uspto-grants-1995_03
Patent number
US05399580

Reaction notes

Loading…