Sodium Hydroxide → 3-[N-(N-benzyloxycarbonylaminoacetyl)N-hydroxyamino]propylphosphonic acid

HRID 1706205

반응식

HRID 1706205 반응식
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13](Cl)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:16][NH:17][CH2:18][CH2:19][CH2:20][P:21](=[O:24])([OH:23])[OH:22].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(OCC)C.O.CO>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([N:17]([CH2:18][CH2:19][CH2:20][P:21](=[O:22])([OH:24])[OH:23])[OH:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 3421703-(Hydroxyamino)propylphosphonic acidHCID 516892Sodium Bicarbonate2회HCID 12239759Benzyloxycarbonylaminoacetyl chloride

생성물 1

HCID 539241393-[N-(N-benzyloxycarbonylaminoacetyl)N-hydroxyamino]propylphosphonic acid수율 32.7%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

A solution of N-benzyloxycarbonylaminoacetyl chloride (2.85 g) in ethyl ether (5 ml) was added dropwise to a solution of 3-(N-hydroxyamino)propylphosphonic acid (985 mg) and sodium bicarbonate (1.51 g) in a mixture of water (20 ml) and methanol (20 ml) with stirring under ice-cooling. During the period, the reaction mixture was adjusted to pH 7-8 with 5% aqueous sodium bicarbonate solution. The stirring was continued for an hour, whereafter the mixture was adjusted to pH 10 with 1 N aqueous sodium hydroxide solution and stirred at the same temperature for 45 minutes. The resultant mixture was adjusted to pH 7 and methanol was distilled off under reduced pressure. The resultant aqueous solution was adjusted to pH 2 with 10% hydrochloric acid and washed with ethyl acetate (30 ml), whereafter the solution was adjusted to pH 1 with 105 hydrochloric acid and then extracted twice with n-butanol (30 ml). The combined n-butanol layer was concentrated under reduced pressure to give a residue, which was crystallized from ether to give 3-[N-(N-benzyloxycarbonylaminoacetyl)-N-hydroxyamino]propylphosphonic acid (720 mg) in the form of crystals. MP: 101°-105° C.

후처리

  1. temperaturecooling
  2. waitThe stirring was continued for an hour, whereafter the mixture
  3. stirringstirred at the same temperature for 45 minutes
  4. distillationwas distilled off under reduced pressure
  5. washwashed with ethyl acetate (30 ml), whereafter the solution
  6. extractionextracted twice with n-butanol (30 ml)
  7. concentrationThe combined n-butanol layer was concentrated under reduced pressure
  8. customto give a residue, which
  9. customwas crystallized from ether

출처 및 근거

ORD 기록
ord-5895d338b2bc419cb42d1db41d4d9a11
출처 데이터셋
uspto-grants-1980_06
특허 번호
US04206156

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