Sodium Azide → 2-Azido-2-(4-nitrophenyl)ethan-1-ol

HRID 641120

Reaktionsgleichung

Reaktionsgleichung von HRID 641120
[N-:1]=[N+:2]=[N-:3].[Na+].[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C@@H:12]2[O:14][CH2:13]2)=[CH:10][CH:9]=1)([O-:7])=[O:6].N(C[C@@H](C1C=CC([N+]([O-])=O)=CC=1)O)=[N+]=[N-]>C1N(CCCS(O)(=O)=O)CCOC1.C(OCC)C>[N:1]([CH:12]([C:11]1[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:16][CH:15]=1)[CH2:13][OH:14])=[N+:2]=[N-:3]

Komponenten

6

Edukt 3

HCID 33557Sodium AzideHCID 1237169(S)-2-(4-Nitrophenyl)oxiraneHCID 11481186(R)-1-Para-Nitro-Phenyl-2-Azido-Ethanol

Produkt 1

HCID 178204212-Azido-2-(4-nitrophenyl)ethan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 70807MopsLösungsmittel

Versuchsvorschrift

To 60 ml of MOPS buffer (50 mM, pH=7.0), 0.47 gram (3.2 mmol) of racemic para-nitro styrene oxide was added and the suspension was stirred for 60 min. The halohydrin dehalogenase, obtained as described in Example 1, (29 mg in 6 ml buffer) was added. A prepared stock solution of 0.12 gram (1.6 mmol) NaN3 in 5 ml MOPS buffer was slowly added over a period of 24 hours. The reaction was stopped and the suspension was three times extracted with diethylether. After separating, the organic phase was dried with MgSO4, and removed by rotary evaporator yielding an orange oil. This mixture was redissolved in diethylether and the composition and e.e. of the products were determined by chiral HPLC. The mixture mainly consisted of (S)-para-nitro styrene oxide in 46% yield (98% e.e.) and (R)-2-azido-1-(para-nitrophenyl)ethanol in 47% yield (97% e.e.). The chemical side product 2-azido-2-(para-nitrophenyl)ethanol was formed to a total of 4% of the reaction mixture. The product of chemical hydrolysis of the epoxide, para-nitrophenyl ethanediol was formed in 3%. All the mentioned yields are calculated yields. Flash chromatography on silica 60H using heptane/ethylacetate (ratio 7:3) as eluent yielded pure epoxide and azido alcohols. The NMR data were identical with synthesized racemic reference compounds.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with diethylether
  3. customAfter separating
  4. dry with materialthe organic phase was dried with MgSO4
  5. customremoved by rotary evaporator
  6. customyielding an orange oil

Quellen und Nachweise

ORD-Eintrag
ord-4d16ef32435c430daf5696c1aa54fded
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07695942B2

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