Sodium Bicarbonate → HCID 178482881, 화합물

HRID 1879662

반응식

HRID 1879662 반응식
[CH3:1][N:2]([C:4]1[C:9]2[CH2:10][C@@H:11]3[C:21]([C:22](=[O:23])[C:8]=2[C:7]([OH:33])=[CH:6][CH:5]=1)=[C:20]([OH:24])[C@@:19]1([OH:25])[C@H:13]([C@H:14]([N:30]([CH3:32])[CH3:31])[C:15]([OH:29])=[C:16]([C:26]([NH2:28])=[O:27])[C:17]1=[O:18])[CH2:12]3)[CH3:3].Cl.C([O-])(O)=O.[Na+]>O>[CH3:3][N:2]([C:4]1[C:9]2[CH2:10][C@@H:11]3[C:21]([C:22](=[O:23])[C:8]=2[C:7]([OH:33])=[CH:6][CH:5]=1)=[C:20]([OH:24])[C@@:19]1([OH:25])[C@H:13]([C@H:14]([N:30]([CH3:32])[CH3:31])[C:15]([OH:29])=[C:16]([C:26]([NH2:28])=[O:27])[C:17]1=[O:18])[CH2:12]3)[CH3:1]

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 178482882HCID 178482882, 화합물

생성물 1

HCID 178482881HCID 178482881, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Minocycline/HCl salt (200 g, 0.406 mol) was suspended in 3 L water and an amount of NaHCO3 (34 g, 0.406 mol) was added in 3 portions and the pH was adjusted to 6.5-7.0. The solution was then extracted with 2×1.5 L CH2Cl2. The solution was concentrated to dryness to give minocycline as the freebase, then redissolved in THF (1.6 L) and was charged in a 3 L 3-necked flask equipped with an over-head stirrer and a temperature probe while under argon. An amount of methyl iodide (289 g, 2.03 mol) was added and the solution was heated at 40-45° C. for approximately 16 hours, at which point it was verified by HPLC that no minocycline was left in solution. The solution was then poured into 6 L of heptane while on ice bath and stirred for at least 20 minutes at <5° C. The precipitate was filtered and washed with hexane (400 mL). The solid was dried under reduced pressure to a constant weight. An amount of 186 g methylammonium salt of minocycline was isolated.

후처리

  1. extractionThe solution was then extracted with 2×1.5 L CH2Cl2
  2. concentrationThe solution was concentrated to dryness

출처 및 근거

ORD 기록
ord-dba3590bf6b344a6b7bcd910bdd75f5d
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318706B2

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