(1S,2S,4S)-4-{[(tert-butoxy)carbonyl]amino}-4-[1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl]cyclohexaneacetic acid

Base Information

• Chemical Name: (1S,2S,4S)-4-{[(tert-butoxy)carbonyl]amino}-4-[1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl]cyclohexaneacetic acid
• CAS No.: 221301-17-3
• Molecular Formula: C₁₈H₂₇N₃O₆
• Molecular Weight: 381.429

Synonyms:(1S,2S,4S)-4-{[(tert-butoxy)carbonyl]amino}-4-[1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl]cyclohexaneacetic acid

Chemical Property of (1S,2S,4S)-4-{[(tert-butoxy)carbonyl]amino}-4-[1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl]cyclohexaneacetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4S)-4-{[(tert-butoxy)carbonyl]amino}-4-[1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl]cyclohexaneacetic acid

There total 17 articles about (1S,2S,4S)-4-{[(tert-butoxy)carbonyl]amino}-4-[1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl]cyclohexaneacetic 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: 94.0%

(1S,3S,4S)-4-{3-[(benzyloxy)methyl]-1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl}-3-{[(tert-butoxy)carbonyl]amino}cyclohexane acetic acid (221301-03-7) → (1S,2S,4S)-4-{[(tert-butoxy)carbonyl]amino}-4-[1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl]cyclohexaneacetic acid (221301-17-3)

Guidance literature:

(1S,3S,4S)-4-{3-[(benzyloxy)methyl]-1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl}-3-{[(tert-butoxy)carbonyl]amino}cyclohexane acetic acid; With hydrogen; palladium on activated charcoal; In tetrahydrofuran;

With air; sodium methylate; In methanol;

DOI:10.1002/1522-2675(20000607)83:6<1049::AID-HLCA1049>3.0.CO;2-1

Reference yield:

(S)-(-)-methyl 3-cyclohexene-1-carboxylate (6493-77-2,49543-03-5,68000-20-4,68000-21-5) → (1S,2S,4S)-4-{[(tert-butoxy)carbonyl]amino}-4-[1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl]cyclohexaneacetic acid (221301-17-3)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 99 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

2.1: pyridine / 2 h / 0 °C

3.1: dimethylsulfoxide / 1.5 h / 110 - 120 °C

4.1: 88 percent / H₂O / Raney-Cu / dimethylsulfoxide / 17 h / 95 - 105 °C

5.1: CF₃SO₃SiMe₃; Et₃N / pentane / 1 h / 25 °C

5.2: I₂ / diethyl ether / 3 h

6.1: NaH / dimethylformamide / 0.25 h

6.2: 73 percent / dimethylformamide / 22 h / in dark

7.1: 97 percent / NaOMe / methanol / 19 h / 25 °C

8.1: dimethylformamide / 3 h / 80 °C

9.1: 78 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 25 °C

10.1: 86 percent / p-Ts-NHNH₂; p-TsOH / CH₂Cl₂ / 44 h / 25 °C

11.1: 88 percent / pyridine / DMAP / CH₂Cl₂ / 22 h / 25 °C

12.1: LiOH*H₂O / tetrahydrofuran; H₂O; methanol / 1.33 h / 0 - 25 °C

13.1: 86 percent / Et₃N; DMAP / tetrahydrofuran / 3 h / 25 °C

14.1: 63 percent / 30 percent aq. H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 0.75 h / 0 - 25 °C

15.1: H₂ / 10 percent Pd/C / tetrahydrofuran

15.2: 94 percent / air; NaOMe / methanol

With pyridine; dmap; lithium hydroxide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; water; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; toluene-4-sulfonic acid hydrazide; dmap; palladium on activated charcoal; Raney-Cu; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane; 1.1: Reduction / 2.1: mesylation / 3.1: Substitution / 4.1: Addition / 5.1: silylation / 5.2: iodolactamization / 6.1: Metallation / 6.2: Alkylation / 7.1: Hydrolysis / 8.1: Condensation / 9.1: Acylation / 10.1: Decomposition / 11.1: Acylation / 12.1: Ring cleavage / 13.1: Acylation / 14.1: Ring cleavage / 15.1: Hydrogenolysis / 15.2: Decomposition;

DOI:10.1002/1522-2675(20000607)83:6<1049::AID-HLCA1049>3.0.CO;2-1

Reference yield:

(S)-4-(Hydroxymethyl)cyclohexene (5681-56-1,1679-51-2,5709-99-9,72581-32-9) → (1S,2S,4S)-4-{[(tert-butoxy)carbonyl]amino}-4-[1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl]cyclohexaneacetic acid (221301-17-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: pyridine / 2 h / 0 °C

2.1: dimethylsulfoxide / 1.5 h / 110 - 120 °C

3.1: 88 percent / H₂O / Raney-Cu / dimethylsulfoxide / 17 h / 95 - 105 °C

4.1: CF₃SO₃SiMe₃; Et₃N / pentane / 1 h / 25 °C

4.2: I₂ / diethyl ether / 3 h

5.1: NaH / dimethylformamide / 0.25 h

5.2: 73 percent / dimethylformamide / 22 h / in dark

6.1: 97 percent / NaOMe / methanol / 19 h / 25 °C

7.1: dimethylformamide / 3 h / 80 °C

8.1: 78 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 25 °C

9.1: 86 percent / p-Ts-NHNH₂; p-TsOH / CH₂Cl₂ / 44 h / 25 °C

10.1: 88 percent / pyridine / DMAP / CH₂Cl₂ / 22 h / 25 °C

11.1: LiOH*H₂O / tetrahydrofuran; H₂O; methanol / 1.33 h / 0 - 25 °C

12.1: 86 percent / Et₃N; DMAP / tetrahydrofuran / 3 h / 25 °C

13.1: 63 percent / 30 percent aq. H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 0.75 h / 0 - 25 °C

14.1: H₂ / 10 percent Pd/C / tetrahydrofuran

14.2: 94 percent / air; NaOMe / methanol

With pyridine; dmap; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; water; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; toluene-4-sulfonic acid hydrazide; dmap; palladium on activated charcoal; Raney-Cu; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane; 1.1: mesylation / 2.1: Substitution / 3.1: Addition / 4.1: silylation / 4.2: iodolactamization / 5.1: Metallation / 5.2: Alkylation / 6.1: Hydrolysis / 7.1: Condensation / 8.1: Acylation / 9.1: Decomposition / 10.1: Acylation / 11.1: Ring cleavage / 12.1: Acylation / 13.1: Ring cleavage / 14.1: Hydrogenolysis / 14.2: Decomposition;

DOI:10.1002/1522-2675(20000607)83:6<1049::AID-HLCA1049>3.0.CO;2-1

upstream raw materials:

(1S,3S,4S)-4-{3-[(benzyloxy)methyl]-1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl}-3-{[(tert-butoxy)carbonyl]amino}cyclohexane acetic acid

di-tert-butyl dicarbonate

(S)-(-)-methyl 3-cyclohexene-1-carboxylate

(S)-4-(Hydroxymethyl)cyclohexene

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