N⁴-(cyclohexylmethyl)-N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide

Base Information

• Chemical Name: N⁴-(cyclohexylmethyl)-N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide
• CAS No.: 225378-79-0
• Molecular Formula: C₄₂H₆₃Cl₃N₆O₇S
• Molecular Weight: 902.423
• Mol file: 225378-79-0.mol

Synonyms:N⁴-(cyclohexylmethyl)-N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide

Chemical Property of N⁴-(cyclohexylmethyl)-N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-(cyclohexylmethyl)-N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide

There total 13 articles about N⁴-(cyclohexylmethyl)-N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide 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: 54.0%

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (122621-77-6) + N-cyclohexylmethyl-N-{[methyl-(2-pyridin-2-yl-ethyl)-carbamoyl]-methyl}-2-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-ylmethyl]-succinamic acid → N4-(cyclohexylmethyl)-N1-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N4-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide + N4-(cyclohexylmethyl)-N1-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N4-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide (225378-79-0)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; for 3.5h; Yields of byproduct given;

DOI:10.1016/S0968-0896(98)00265-X

Reference yield:

ethyl 2-<(cyclohexylmethyl)amino>acetate (144006-28-0) → N4-(cyclohexylmethyl)-N1-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N4-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide (225378-79-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / CH₂Cl₂ / 2.5 h / 25 °C

2: 96 percent / 2N NaOH / methanol / 16 h / 25 °C

3: 89 percent / BOP*PF₆, i-Pr₂NEt / dimethylformamide / 3 h / 25 °C

4: 95 percent / 4N HCl / dioxane / 1 h / 25 °C

5: 88 percent / i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 25 h / 25 °C

6: 90 percent / Mg(OMe)2 / 1 h / 0 °C

7: 99 percent / 2N NaOH / tetrahydrofuran; methanol; H₂O / 14 h / 25 °C

8: 54 percent / i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 3.5 h / 25 °C

With hydrogenchloride; sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; magnesium methanolate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(98)00265-X

Reference yield:

3-(5-bromo-1,4-dioxopentyl)-4(S)-(1-methylethyl)-2-oxazolidinone (160447-17-6) → N4-(cyclohexylmethyl)-N1-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N4-<2-amino>-2-oxoethyl>-2(R)-<<2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolyl>methyl>butanediamide (225378-79-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 55 percent / tetrahydrofuran / 25 °C

2: 4.23 g / thiourea / propan-2-ol / 0.5 h / Heating

3: 61 percent / i-Pr₂NEt, DMAP / CH₂Cl₂ / 1.) 0 deg C, 45 min, 2.) 25 deg C, 16 h

4: 59 percent / NaHMDS / tetrahydrofuran / -78 °C / 1.) 45 min, 2.) 2 h

5: TFA / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 25 deg C, 3 h

6: 88 percent / i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 25 h / 25 °C

7: 90 percent / Mg(OMe)2 / 1 h / 0 °C

8: 99 percent / 2N NaOH / tetrahydrofuran; methanol; H₂O / 14 h / 25 °C

9: 54 percent / i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 3.5 h / 25 °C

With dmap; sodium hydroxide; sodium hexamethyldisilazane; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; magnesium methanolate; N-ethyl-N,N-diisopropylamine; thiourea; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/S0968-0896(98)00265-X

upstream raw materials:

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

ethyl 2-<(cyclohexylmethyl)amino>acetate

3-(5-bromo-1,4-dioxopentyl)-4(S)-(1-methylethyl)-2-oxazolidinone

3-<1-oxo-3-(4-thiazolyl)propyl>-4(S)-(1-methylethyl)-2-oxazolidinone

Downstream raw materials:

BILA 2157 BS