rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N⁶-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide

Base Information

• Chemical Name: rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N⁶-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide
• CAS No.: 255735-96-7
• Molecular Formula: C₃₆H₄₁ClN₈O₆
• Molecular Weight: 717.225

Synonyms:rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N⁶-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide

Chemical Property of rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N⁶-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide

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Technology Process of rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N⁶-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide

There total 3 articles about rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N⁶-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide 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: 78.0%

N-BOC-1,2-diaminoethane (57260-73-8) + 1-isocyanocyclohexene (1121-57-9) + 2-chloro-benzaldehyde (89-98-5) + [6-N-(benzyloxycarbonyl)-adenin-9-yl]-acetic acid (149376-67-0) → rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N6-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide (255735-96-7)

Guidance literature:

In methanol; at 20 ℃; for 48h;

DOI:10.1016/S0968-0896(00)00066-3

Reference yield:

N-(cyclohexen-1-yl)formamide (40652-40-2) → rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N6-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide (255735-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / phosgene; NEt₃ / CH₂Cl₂ / 1 h / 0 °C

2: 78 percent / methanol / 48 h / 20 °C

With phosgene; triethylamine; In methanol; dichloromethane; 1: Dehydration / 2: Ugi four component condensation;

DOI:10.1016/S0968-0896(00)00066-3

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N6-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide (255735-96-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / aq. H₂SO₄ / toluene / 12 h / Heating; Dean-Stark-conditions

2: 71 percent / phosgene; NEt₃ / CH₂Cl₂ / 1 h / 0 °C

3: 78 percent / methanol / 48 h / 20 °C

With phosgene; sulfuric acid; triethylamine; In methanol; dichloromethane; toluene; 1: Condensation / 2: Dehydration / 3: Ugi four component condensation;

DOI:10.1016/S0968-0896(00)00066-3

upstream raw materials:

N-BOC-1,2-diaminoethane

1-isocyanocyclohexene

2-chloro-benzaldehyde

[6-N-(benzyloxycarbonyl)-adenin-9-yl]-acetic acid

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