Phosphoethanolamine → Mitomycin phosphate

HRID 1110452

反応式

HRID 1110452 の反応式
[P:1]([OH:8])([OH:7])([O:3][CH2:4][CH2:5][NH2:6])=[O:2].C(N(CC)CC)C.[CH3:16][C:17]1[C:23](=[O:24])[C:22]2[N:25]3[C@@:29]([O:36][CH3:37])([C@H:30]([CH2:31][O:32][C:33]([NH2:35])=[O:34])[C:21]=2[C:19](=[O:20])[C:18]=1OC)[C@H:28]1[NH:38][C@H:27]1[CH2:26]3.C(=O)(O)[O-].[Na+]>O.CO>[CH3:16][C:17]1[C:23](=[O:24])[C:22]2[N:25]3[C@@:29]([O:36][CH3:37])([C@H:30]([CH2:31][O:32][C:33]([NH2:35])=[O:34])[C:21]=2[C:19](=[O:20])[C:18]=1[NH:6][CH2:5][CH2:4][O:3][P:1]([OH:8])([OH:7])=[O:2])[C@H:28]1[NH:38][C@H:27]1[CH2:26]3

参加物

7

反応物 4

HCID 1015PhosphoethanolamineHCID 8471TriethylamineHCID 19972Mitomycin AHCID 516892Sodium Bicarbonate

生成物 1

HCID 130219Mitomycin phosphate

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of 2-aminoethyl dihydrogen phosphate (56 mg, 0.4 mmol) in water (0.35 ml) and triethylamine (0.3 ml, 2 mmol) was added to mitomycin A (referred to hereinafter as "MMA") (140 mg, 0.4 mmol) in methanol (6 ml) and the reaction was allowed to proceed at room temperature overnight. 1.4 ml of saturated aqueous sodium bicarbonate was then added and the solution was partitioned between water and methylene chloride. The aqueous phase was concentrated to dryness and several portions of methanol were added and evaporated. The residue was taken up into methanol, filtered, and applied to a 2×10 cm C-18 (reverse phase) silica column. The product was eluted with water and all volatile material was evaporated. Methanol was added and evaporated as before and the residue was dried for 24 h under high vacuum in a desiccator with phosphorus pentoxide. The mitomycin phosphate derivative, MOP, was obtained as a fine blue powder (190 mg, 97%).

後処理

  1. customthe solution was partitioned between water and methylene chloride
  2. concentrationThe aqueous phase was concentrated to dryness and several portions of methanol
  3. additionwere added
  4. customevaporated
  5. filtrationfiltered
  6. washThe product was eluted with water
  7. customall volatile material was evaporated
  8. additionMethanol was added
  9. customevaporated as before and the residue
  10. dry with materialwas dried for 24 h under high vacuum in a desiccator with phosphorus pentoxide

出典と根拠

ORDレコード
ord-292a2b2000f84a3bbef2ad24c573cf89
出典データセット
uspto-grants-1990_12
特許番号
US04975278

関連ノート

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