Hydrogen Bromide → t-Butyl 7alpha-bromo-3-methyl-3-cephem-4carboxylate

HRID 257807노트

반응식

HRID 257807 반응식
N[C@H:2]1[C:17](=[O:18])[N:4]2[C:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12.[BrH:19].N([O-])=O.[Na+].[Cl-].[Na+]>O.C(O)C>[Br:19][C@H:2]1[C:17](=[O:18])[N:4]2[C:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12

참가 물질

7

반응물 4

HCID 260Hydrogen BromideHCID 5234Sodium ChlorideHCID 23668193Sodium NitriteHCID 67657240t-Butyl 7alpha-amino-3-methyl-3-cephem-4-carboxylate

생성물 1

HCID 67656826t-Butyl 7alpha-bromo-3-methyl-3-cephem-4carboxylate수율 50%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To an ice-cooled mixture of t-butyl 7α-amino-3-methyl-3-cephem-4-carboxylate (1.3 g, 0.0048 mol), ethanol (30 ml), water (8.5 ml), hydrobromic acid (48%, 5.83 ml), sodium nitrite (0.48 g, 0.00696 mol) was added portionwise over 15 minutes and the mixture was stirred at ice-temperature (-5° C.) for 3 hours, saturated with sodium chloride, extracted with ethyl acetate (3 times). The combined ethyl acetate extract was washed with water, brine, dried and concentrated to give 800 mg (50%) of pure t-butyl 7α-bromo-3-methyl-3-cephem-4carboxylate.

후처리

  1. additionwas added portionwise over 15 minutes
  2. extractionextracted with ethyl acetate (3 times)
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water, brine
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8e2058d19a8645c49811053e138be1e2
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264430

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