2-(2-Carboxy-3-methoxymethylcyclopropyl)glycine

Base Information

• Chemical Name: 2-(2-Carboxy-3-methoxymethylcyclopropyl)glycine
• CAS No.: 130532-53-5
• Molecular Formula: C₈H₁₃NO₅
• Molecular Weight: 203.195
• DSSTox Substance ID: DTXSID50926786
• Nikkaji Number: J731.654B
• Wikidata: Q82901395
• Mol file: 130532-53-5.mol

Synonyms:2-(2-carboxy-3-methoxymethylcyclopropyl)glycine;cis-MCG-I;trans-MCG-I

Chemical Property of 2-(2-Carboxy-3-methoxymethylcyclopropyl)glycine

Chemical Property:

• Vapor Pressure: 5.14E-08mmHg at 25°C
• Boiling Point: 414°Cat760mmHg
• Flash Point: 204.2°C
• PSA: 109.85000
• Density: 1.417g/cm³
• LogP: -0.30820
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 203.07937252
• Heavy Atom Count: 14
• Complexity: 254

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC1C(C1C(=O)O)C(C(=O)O)N
• Isomeric SMILES: COC[C@H]1[C@@H]([C@@H]1C(=O)O)[C@@H](C(=O)O)N

Technology Process of 2-(2-Carboxy-3-methoxymethylcyclopropyl)glycine

There total 8 articles about 2-(2-Carboxy-3-methoxymethylcyclopropyl)glycine 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:

2-Amino-1-{(S)-4-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-2,2-dimethyl-oxazolidin-3-yl}-ethanone → (1S,2S,3S)-2-((S)-Amino-carboxy-methyl)-3-methoxymethyl-cyclopropanecarboxylic acid (130532-53-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) NaNO₂, citric acid / 2) Pd(OAc)2 / 1) toluene, r.t., 20 min 2) toluene, 90 deg C, 30 min

2: nBu₄NF / tetrahydrofuran / 0.17 h / 0 °C

3: NaH, nBu₄NI / 2 h / Ambient temperature

4: 1) 60percent HOAc 2) Ba(OH)2 / 1) r.t., 12 h 2) EtOH, H₂O, 80 deg C, 14 h

5: Et₃N / dioxane / 16 h / Ambient temperature

6: Jones oxidation

7: TFA

With barium dihydroxide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; trifluoroacetic acid; citric acid; sodium nitrite; palladium diacetate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0040-4039(00)94496-4

Reference yield:

(2-{(S)-4-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-propenyl]-2,2-dimethyl-oxazolidin-3-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester (130532-56-8) → (1S,2S,3S)-2-((S)-Amino-carboxy-methyl)-3-methoxymethyl-cyclopropanecarboxylic acid (130532-53-5)

Guidance literature:

Multi-step reaction with 8 steps

1: trimethylsilyl trifluoromethanesulfonate (TMSOTf), 2,6-lutidine / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 1) NaNO₂, citric acid / 2) Pd(OAc)2 / 1) toluene, r.t., 20 min 2) toluene, 90 deg C, 30 min

3: nBu₄NF / tetrahydrofuran / 0.17 h / 0 °C

4: NaH, nBu₄NI / 2 h / Ambient temperature

5: 1) 60percent HOAc 2) Ba(OH)2 / 1) r.t., 12 h 2) EtOH, H₂O, 80 deg C, 14 h

6: Et₃N / dioxane / 16 h / Ambient temperature

7: Jones oxidation

8: TFA

With 2,6-dimethylpyridine; barium dihydroxide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; trifluoroacetic acid; citric acid; sodium nitrite; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/S0040-4039(00)94496-4

Reference yield:

(1S,2S,3S)-2-((S)-1-Amino-2-hydroxy-ethyl)-3-methoxymethyl-cyclopropanecarboxylic acid → (1S,2S,3S)-2-((S)-Amino-carboxy-methyl)-3-methoxymethyl-cyclopropanecarboxylic acid (130532-53-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / dioxane / 16 h / Ambient temperature

2: Jones oxidation

3: TFA

With triethylamine; trifluoroacetic acid; In 1,4-dioxane;

DOI:10.1016/S0040-4039(00)94496-4

upstream raw materials:

(1S,1aS,1bS,5aS)-1-Hydroxymethyl-4,4-dimethyl-tetrahydro-3-oxa-4a-aza-cyclopropa[a]pentalen-5-one

(1S,1aS,1bS,5aS)-1-Methoxymethyl-4,4-dimethyl-tetrahydro-3-oxa-4a-aza-cyclopropa[a]pentalen-5-one

(1S,1aS,1bS,5aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3-oxa-4a-aza-cyclopropa[a]pentalen-5-one

(1S,2S,3S)-2-((S)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-3-methoxymethyl-cyclopropanecarboxylic acid

Refernces