Sodium Chloride → 3-Acetoxymethyl-7-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

HRID 258003노트

반응식

HRID 258003 반응식
N[C@@H:2]1[C:21](=[O:22])[N:4]2[C:5]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH2:7][S:8][C@H:3]12.N([O-])=O.[Na+].[Cl-:27].[Na+]>C(O)C.O.Cl>[Cl:27][C@H:2]1[C:21](=[O:22])[N:4]2[C:5]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH2:7][S:8][C@H:3]12

참가 물질

7

반응물 3

HCID 5234Sodium ChlorideHCID 15573427tert-butyl (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 23668193Sodium Nitrite

생성물 1

HCID 157268683-Acetoxymethyl-7-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester수율 73%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 962Water용매

실험 절차

To an ice-cooled solution of t-butyl 7β-amino-3-acetoxymethyl-3-cephem-4-carboxylate (4.0 g, 0.0122 mol) in 75 ml of ethanol, 16.7 ml of water and 16.7 ml of concentrated hydrochloric acid and sodium nitrite (1.18 g, 0.017 mol) were added portionwise over 15-20 minutes. The reaction mixture was stirred at 0°-5° C. for 2.5 hours, saturated with sodium chloride, extracted with methylene chloride, washed with water, brine, dried (Na2SO4) and concentrated to give 3.1 g (73%) of t-butyl 7α-chloro-3-acetoxymethyl-3-cephem-4-carboxylate.

후처리

  1. additionwere added portionwise over 15-20 minutes
  2. extractionextracted with methylene chloride
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-32eec04832814a32900bd076cb840730
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264429

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