3-(7-oxo-1-aza-4-oxabicyclo(3.2.0)hept-3-yl)alanine

Base Information

• Chemical Name: 3-(7-oxo-1-aza-4-oxabicyclo(3.2.0)hept-3-yl)alanine
• CAS No.: 74758-63-7
• Molecular Formula: C₈H₁₂N₂O₄
• Molecular Weight: 200.194
• Hs Code.: 2934999090
• Mol file: 74758-63-7.mol

Synonyms:4-Oxa-1-azabicyclo[3.2.0]heptane-3-propanoicacid, a-amino-7-oxo-, [3S-[3a(R*),5a]]-; Alanylclavam; Clavalanine; Ro 22-5417

Chemical Property of 3-(7-oxo-1-aza-4-oxabicyclo(3.2.0)hept-3-yl)alanine

Chemical Property:

• Vapor Pressure: 4.14E-09mmHg at 25°C
• Boiling Point: 443.6°C at 760 mmHg
• Flash Point: 222.1°C
• PSA: 92.86000
• Density: 1.49g/cm³
• LogP: -0.61620

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(7-oxo-1-aza-4-oxabicyclo(3.2.0)hept-3-yl)alanine

There total 17 articles about 3-(7-oxo-1-aza-4-oxabicyclo(3.2.0)hept-3-yl)alanine 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: 96.7%

3-<(3S,5S)-7-oxo-1-aza-4-oxabicyclo<3.2.0>hept-3-yl>-N-(benzyloxycarbonyl)-L-alanine diphenylmethyl ester (97551-74-1) → Clavalanine (74758-63-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 3h; under 760 Torr; Ambient temperature;

DOI:10.1021/jo00219a008

Reference yield:

5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose (80244-96-8) → Clavalanine (74758-63-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 97.3 percent / 1,2-dichloro-ethane / 1 h / Heating

2: 95 percent / Bu3SnH, α,α'-azobis(isobutyronitrile) (AIBN) / toluene / 1 h / Heating

3: 60.9 percent / trifluoroacetic acid (TFA) / 1.25 h / 5 °C

4: 1.) dibutyltin oxide, 2.) Et₃N / 1.) MeOH, reflux, 1.5 h, 2.) 1,2-dimethoxyethane, 4 deg C, 1 h

5: 98 percent / RuO₄ / 1,2-dichloro-ethane / 1 h / 4 - 20 °C

6: 90.1 percent / LiN₃ / dimethylformamide / Ambient temperature

7: 51 percent / H₂, HCl / 10percent Pd/C / ethanol / 0.75 h / 760 Torr

8: 90.5 percent / NaHCO₃ / H₂O; diethyl ether / 2.5 h / 4 - 20 °C

9: 93.4 percent / Dowex AG 50W-X₄ (H⁺) / dioxane; H₂O / 24 h / 73 - 75 °C

10: 1.) 0.1 N aq. KOH, 2.) Dowex AG 50W-X₄ (H⁺) / 1.) 20 deg C, 1 h

11: 78.3 percent / methyl acetate / 4 h / Ambient temperature

12: 62.6 percent / pyridine, 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 5 h, 2.) RT, 15 h

13: 51.5 percent / Pd(OAc)2, NEt₃ / benzene / 38 h / Ambient temperature

14: 94.9 percent / LiBr / tetrahydrofuran / 6.5 h / Heating

15: 50 percent / 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadienoate / dimethylformamide / 10 h / 70 °C

16: 96.7 percent / H₂ / 10percent Pd/C / methanol / 3 h / 760 Torr / Ambient temperature

With pyridine; hydrogenchloride; dmap; palladium diacetate; potassium hydroxide; ruthenium tetroxide; lithium azide; 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadienoate; Dowex AG 50W-X₄ (H⁺); azobisisobutyronitrile; hydrogen; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; acetic acid methyl ester; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00219a008

Reference yield:

(3S,5S)-3-benzyloxycarbonylamino-5-hydroxy-γ-lactone (97551-67-2) → Clavalanine (74758-63-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 0.1 N aq. KOH, 2.) Dowex AG 50W-X₄ (H⁺) / 1.) 20 deg C, 1 h

2: 78.3 percent / methyl acetate / 4 h / Ambient temperature

3: 62.6 percent / pyridine, 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 5 h, 2.) RT, 15 h

4: 51.5 percent / Pd(OAc)2, NEt₃ / benzene / 38 h / Ambient temperature

5: 94.9 percent / LiBr / tetrahydrofuran / 6.5 h / Heating

6: 50 percent / 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadienoate / dimethylformamide / 10 h / 70 °C

7: 96.7 percent / H₂ / 10percent Pd/C / methanol / 3 h / 760 Torr / Ambient temperature

With pyridine; dmap; palladium diacetate; potassium hydroxide; 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadienoate; Dowex AG 50W-X₄ (H⁺); hydrogen; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid methyl ester; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00219a008

upstream raw materials:

3-<(3S,5S)-7-oxo-1-aza-4-oxabicyclo<3.2.0>hept-3-yl>-N-(benzyloxycarbonyl)-L-alanine diphenylmethyl ester

5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose

(3S,5S)-3-benzyloxycarbonylamino-5-hydroxy-γ-lactone

1,2-O-isopropylidene-α-D-xylose