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

HRID 257807ノート

反応式

HRID 257807 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8e2058d19a8645c49811053e138be1e2
出典データセット
uspto-grants-1993_11
特許番号
US05264430

反応ノート

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