(2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Base Information

Chemical Name:(2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole
CAS No.:305322-35-4
Molecular Formula:C₃₀H₃₄N₄O₆
Molecular Weight:546.623
Hs Code.:

(2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Synonyms:(2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

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Chemical Property of (2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

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Technology Process of (2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

There total 8 articles about (2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole 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: 84.0%

: 2577-90-4
methyl (2S)-2-amino-3-phenylpropanoate

: 305322-32-1
(2R,,5R,11bS)-2-(tert-butoxycarbonyl)amino-5-carboxy-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

: 305322-35-4
(2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Guidance literature:: With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane; at 20 ℃;
DOI:10.1021/jm000959x

Reference yield:

: 92828-64-3
(R)-2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester

: 305322-35-4
(2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Guidance literature:: Multi-step reaction with 8 steps

1: NMM / tetrahydrofuran / 0.17 h / -15 °C

2: NaBH₄ / H₂O / -10 °C

3: 84 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

4: 68 percent / TFA / toluene / 20 °C

5: 98 percent / H₂ / 10percent Pd/C / methanol / 2 h / 20 °C / 1551.49 Torr

6: 93 percent / xylene / 2 h / Heating

7: 93 percent / 2N NaOH / methanol / 18 h / 20 °C

8: 84 percent / BOP; TEA / CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; TEA; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimethyl sulfoxide; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; water; toluene; xylene;
DOI:10.1021/jm000959x

Reference yield:

: (R)-2-tert-Butoxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester

: 305322-35-4
(2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Guidance literature:: Multi-step reaction with 7 steps

1: NaBH₄ / H₂O / -10 °C

2: 84 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

3: 68 percent / TFA / toluene / 20 °C

4: 98 percent / H₂ / 10percent Pd/C / methanol / 2 h / 20 °C / 1551.49 Torr

5: 93 percent / xylene / 2 h / Heating

6: 93 percent / 2N NaOH / methanol / 18 h / 20 °C

7: 84 percent / BOP; TEA / CH₂Cl₂ / 20 °C

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; TEA; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimethyl sulfoxide; trifluoroacetic acid; 10percent Pd/C; In methanol; dichloromethane; water; toluene; xylene;
DOI:10.1021/jm000959x