(3aR,4R,6S,6aS)-4-(tert-butoxycarbonylaMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylic acid

Base Information

• Chemical Name: (3aR,4R,6S,6aS)-4-(tert-butoxycarbonylaMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylic acid
• CAS No.: 316173-28-1
• Molecular Formula: C17H28N2O5 . C4H11N
• Molecular Weight: 413.55100
• Mol file: 316173-28-1.mol

Synonyms:4H-Cyclopent[d]isoxazole-6-carboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1-ethylpropyl)-3a,5,6,6a-tetrahydro-, (3aR,4R,6S,6aS)-, compd. with 2-methyl-2-propanamine (1:1) (9CI);2-Propanamine, 2-methyl-, (3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylate (9CI);

Chemical Property of (3aR,4R,6S,6aS)-4-(tert-butoxycarbonylaMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylic acid

Chemical Property:

• PSA: 126.73000
• LogP: 3.87530

Purity/Quality:

98% ^*data from raw suppliers

2-Methylpropan-2-aminium(3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3aR,4R,6S,6aS)-4-(tert-butoxycarbonylaMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylic acid

There total 2 articles about (3aR,4R,6S,6aS)-4-(tert-butoxycarbonylaMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylic acid 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: 91.5%

(3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1'-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic acid + tert-butylamine (75-64-9) → (3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1'-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic acid tert-butylamine (316173-28-1)

Guidance literature:

In dichloromethane; at 5 ℃; for 2h; Temperature;

Reference yield: 62.0%

tert-butylamine (75-64-9) + 2-ethyl-N-hydroxybutanimidoyl chloride + (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate (168683-02-1) → (3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1'-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic acid tert-butylamine (316173-28-1)

Guidance literature:

2-ethyl-N-hydroxybutanimidoyl chloride; (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate; With triethylamine; In toluene; at 50 - 66 ℃; for 10.5h; Industry scale;

With water; sodium hydroxide; In toluene; at 20 ℃; for 7h;

tert-butylamine;

Reference yield: 97.13%

(3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1'-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic acid tert-butylamine (316173-28-1) + dimethyl sulfate (77-78-1) → (+)-methyl (3aR,4R,6S,6aS)-4-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate (229613-93-8)

Guidance literature:

(3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1'-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic acid tert-butylamine; With potassium carbonate; sodium hydroxide; In water; acetone; Industry scale;

dimethyl sulfate; In water; acetone; at 30 - 45 ℃;

With ammonia; In methanol; water; acetone; at 0 - 20 ℃; for 1.25h; Industry scale;

upstream raw materials:

tert-butylamine

(1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate

Downstream raw materials:

(+)-methyl (3aR,4R,6S,6aS)-4-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate

Refernces

• 1、 -. "(1S, 2S, 3S, 4R)-3-Y(1S)-1-ACETYLAMINO-2-ETHYL-BUTYL¨-4-GUANIDINO-2- HYDROXYL-CYCLOPENTYL-1-CARBOXYLIC ACID HYDRATES AND PHARMACEUTICAL USES THEREOF". Page/Page column 11. . Retrieved 2010/06/15.