N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester

Base Information

Chemical Name:N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester
CAS No.:603128-68-3
Molecular Formula:C₁₇H₂₉ClN₂O₅
Molecular Weight:376.881
Hs Code.:

Synonyms:N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester

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Chemical Property of N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester

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Technology Process of N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester

There total 11 articles about N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester 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: 73.0%

: 79-04-9
chloroacetyl chloride

: 603128-66-1
N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]glycine ethyl ester

: 603128-68-3
N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester

Guidance literature:: With sodium carbonate; In 1,4-dioxane; water; at 0 ℃; for 0.5h;
DOI:10.1021/ol034933m

Reference yield:

: trans-2-azido-1-cyclohexanol

: 603128-68-3
N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine; DMAP / 16 h / 20 °C

2: lipase Amano-PS; aq. phosphate buffer / 2.5 h / pH 7.2

3: 92.6 percent / H₂ / PtO₂ / ethyl acetate / 3 h / 20 °C / 1810.02 - 2068.59 Torr

4: 97.9 percent / pyridine; DMAP / 0 °C

5: 87 percent / NaN₃ / dimethylformamide / 12 h / 65 - 70 °C

6: H₂ / PtO₂ / methanol / 3 h / 20 °C / 1810.02 - 2068.59 Torr

7: 76.6 percent / KF/Celite / acetonitrile / 3.5 h / 20 °C

8: 73 percent / Na₂CO₃ / dioxane; H₂O / 0.5 h / 0 °C

With pyridine; dmap; potassium fluoride; sodium azide; phosphate buffer; Celite; lipase Amano-PS; hydrogen; sodium carbonate; platinum(IV) oxide; In 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo035747x

Reference yield:

: Butyric acid (1S,2S)-2-azido-cyclohexyl ester

: 603128-68-3
N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: lipase Amano-PS; aq. phosphate buffer / 2.5 h / pH 7.2

2: 92.6 percent / H₂ / PtO₂ / ethyl acetate / 3 h / 20 °C / 1810.02 - 2068.59 Torr

3: 97.9 percent / pyridine; DMAP / 0 °C

4: 87 percent / NaN₃ / dimethylformamide / 12 h / 65 - 70 °C

5: H₂ / PtO₂ / methanol / 3 h / 20 °C / 1810.02 - 2068.59 Torr

6: 76.6 percent / KF/Celite / acetonitrile / 3.5 h / 20 °C

7: 73 percent / Na₂CO₃ / dioxane; H₂O / 0.5 h / 0 °C

With pyridine; dmap; potassium fluoride; sodium azide; phosphate buffer; Celite; lipase Amano-PS; hydrogen; sodium carbonate; platinum(IV) oxide; In 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo035747x