3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-difluoro-4-oxo-,(1R,2S,5S)-(9CI)

Base Information

• Chemical Name: 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-difluoro-4-oxo-,(1R,2S,5S)-(9CI)
• CAS No.: 201231-48-3
• Molecular Formula: C₆H₅F₂NO₃
• Molecular Weight: 177.107
• Mol file: 201231-48-3.mol

Synonyms:3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-difluoro-4-oxo-,(1R,2S,5S)-(9CI)

Chemical Property of 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-difluoro-4-oxo-,(1R,2S,5S)-(9CI)

Chemical Property:

• Boiling Point: 476.4±45.0 °C(Predicted)
• PKA: 2.58±0.40(Predicted)
• PSA: 0.00000
• Density: 1.71±0.1 g/cm3(Predicted)
• LogP: 0.00000

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-difluoro-4-oxo-,(1R,2S,5S)-(9CI)

There total 13 articles about 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-difluoro-4-oxo-,(1R,2S,5S)-(9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(4S),(Z)-1-benzyloxy-4,5-(isopropylidenedioxy)-2-pentene (128373-65-9) → (1S,2S,5R)-6,6-Difluoro-4-oxo-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid (201231-48-3)

Guidance literature:

Multi-step reaction with 13 steps

1: bis-(2-methoxy-ethyl) ether / 180 °C

2: HCl / methanol

3: imidazole

4: 1.) PhCOOH, DEAD, 2.) 1 N KOH

5: (PhO)2P(O)N₃, DEAD, Ph₃P

6: H₂ / 5percent Pd/C / ethyl acetate

7: NaHCO₃

8: 5percent HCl / methanol

9: NaIO₄, RuCl₃

11: H₂ / Pd(OH)2 / ethyl acetate

12: Jones reagent

13: 10percent aq. HCl / 50 °C

With 1H-imidazole; hydrogenchloride; ruthenium trichloride; potassium hydroxide; sodium periodate; jones reagent; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; triphenylphosphine; benzoic acid; diethylazodicarboxylate; palladium dihydroxide; palladium on activated charcoal; In methanol; diethylene glycol dimethyl ether; ethyl acetate;

DOI:10.1016/S0960-894X(98)00338-2

Reference yield:

(S)-1-((1S,3R)-3-Benzyloxymethyl-2,2-difluoro-cyclopropyl)-ethane-1,2-diol → (1S,2S,5R)-6,6-Difluoro-4-oxo-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid (201231-48-3)

Guidance literature:

Multi-step reaction with 11 steps

1: imidazole

2: 1.) PhCOOH, DEAD, 2.) 1 N KOH

3: (PhO)2P(O)N₃, DEAD, Ph₃P

4: H₂ / 5percent Pd/C / ethyl acetate

5: NaHCO₃

6: 5percent HCl / methanol

7: NaIO₄, RuCl₃

9: H₂ / Pd(OH)2 / ethyl acetate

10: Jones reagent

11: 10percent aq. HCl / 50 °C

With 1H-imidazole; hydrogenchloride; ruthenium trichloride; potassium hydroxide; sodium periodate; jones reagent; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; triphenylphosphine; benzoic acid; diethylazodicarboxylate; palladium dihydroxide; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1016/S0960-894X(98)00338-2

Reference yield:

(S)-4-((1S,3R)-3-Benzyloxymethyl-2,2-difluoro-cyclopropyl)-2,2-dimethyl-[1,3]dioxolane (201230-90-2) → (1S,2S,5R)-6,6-Difluoro-4-oxo-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid (201231-48-3)

Guidance literature:

Multi-step reaction with 12 steps

1: HCl / methanol

2: imidazole

3: 1.) PhCOOH, DEAD, 2.) 1 N KOH

4: (PhO)2P(O)N₃, DEAD, Ph₃P

5: H₂ / 5percent Pd/C / ethyl acetate

6: NaHCO₃

7: 5percent HCl / methanol

8: NaIO₄, RuCl₃

10: H₂ / Pd(OH)2 / ethyl acetate

11: Jones reagent

12: 10percent aq. HCl / 50 °C

With 1H-imidazole; hydrogenchloride; ruthenium trichloride; potassium hydroxide; sodium periodate; jones reagent; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; triphenylphosphine; benzoic acid; diethylazodicarboxylate; palladium dihydroxide; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1016/S0960-894X(98)00338-2

upstream raw materials:

(1S,2S,5R)-6,6-Difluoro-4-oxo-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester 2-methyl ester

(4S),(Z)-1-benzyloxy-4,5-(isopropylidenedioxy)-2-pentene

(S)-4-((1S,3R)-3-Benzyloxymethyl-2,2-difluoro-cyclopropyl)-2,2-dimethyl-[1,3]dioxolane

(S)-tert-Butoxycarbonylamino-((1S,3R)-2,2-difluoro-3-hydroxymethyl-cyclopropyl)-acetic acid methyl ester