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# c12) United States Patent 

# Lee et al. 

# (54) METHOD FOR THE PREPARATION OF D-ERYTHRO-2,2-DIFLUORO-2-DEOXY-1- OXORIBOSE DERIVATIVE 

(75) Inventors: Jaeheon Lee, Yongin-si (KR); Gha-Seung Park, Yongin-si (KR); Moonsub Lee, Daejeon (KR); Cheol-Kyong Kim, Suwon-si (KR); Jae-Chui Lee, Suwon-si (KR); Young-Kil Chang, Seoul (KR); Gwan-Sun Lee, Seoul (KR) 

(73) Assignee: Hanmi Pharm, Co., Ltd, Hwaseong-gun (KR) 

( *) Notice: Subject to any disclaimer, the term ofthis patent is extended or adjusted under 35 U.S.C. 154(b) by 204 days. This patent is subject to a terminal dis› claimer. 

(21) Appl. No.: 11/572,404 

(22) PCT Filed: Jun.23,2005 

(86) PCT No.: PCT /KR2005/001955 § 371 (c)(l), (2), ( 4) Date: Jan.19,2007 

(87) PCT Pub. No.: WO2006/009353 

PCT Pub. Date: Jan. 26, 2006 

## (65) Prior Publication Data 

US 2008/0058509 Al Mar. 6, 2008 

## (30) Foreign Application Priority Data 

Jul. 23, 2004 (KR) ...................... 10-2004-0057711 

<img src='content_image/926788.jpg'>

# (IO) Patent No.: US 7,638,642 B2 

# (45) Date of Patent: *Dec. 29, 2009 

(51) Int. Cl. C07D 307102 (2006.01) 

(52) U.S. Cl. ...................................................... 549/477 

(58) Field of Classification Search ....................... None See application file for complete search history. 

## (56) References Cited 

<img src='content_image/926775.jpg'>

Corey et al. Journal of the American Chemical Society 93:6, Mar. 24, 1971, pp. 1491-1493.* 

Greene et al. Protective Groups in Organic Synthesis, Third Edition. John Wily & Sons, 1999, pp. 150-160.* 

* cited by examiner 

Primary Examiner-Shaojia Anna Jiang 

Assistant Examiner-Layla Bland 

(74) Attorney, Agent, or Firm-Sughrue Mion, PLLC 

## (57) ABSTRACT 

3R-carboxylate enantiomer derivative of formula (III) can be prepared easily and selectively by the method of the present invention, and a highly pure D-erythro-2,2-difluoro-2-deoxy› l-oxoribose derivative can be prepared efficiently from the compound of formula (III) as an intermediate. 

US007638642B2 

## U.S. PATENT DOCUMENTS 

## OTHER PUBLICATIONS 

## 8 Claims, No Drawings 

