ChemicalBook CAS DataBase List (S)-4-(3-((tert-butoxycarbonyl)amino)-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate

(S)-4-(3-((tert-butoxycarbonyl)amino)-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate synthesis

6synthesis methods

Product Name:(S)-4-(3-((tert-butoxycarbonyl)amino)-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate
CAS Number:1253955-19-9
Molecular formula:C33H35N3O5
Molecular Weight:553.65

73401-74-8 Synthesis

73401-74-8
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(S)-4-(3-((tert-butoxycarbonyl)amino)-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate

1253955-19-9
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Yield:-

Steps:

Multi-step reaction with 8 steps
1.1: sulfuric acid / 0 - 20 °C / Large scale
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h / 20 °C / Large scale
2.2: 20 °C / Large scale
3.1: water; lithium hydroxide / tetrahydrofuran / 2.5 h / Large scale
4.1: oxalyl dichloride / dichloromethane / 18 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran; n-heptane / 0.5 h / -70 - -65 °C
6.1: lithium hexamethyldisilazane / tetrahydrofuran; n-heptane / 0.67 h / -70 - -65 °C
6.2: 1.5 h / -30 °C
7.1: water; lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran / -5 °C
8.1: 2,2,2-trichloro-1,1-dimethylethoxychloroformate / N,N-dimethyl-formamide / 1 h / 0 - 10 °C

References:

AERIE PHARMACEUTICALS, INC.;STURDIVANT, Jill, M.;DELONG, Mitchell, A.;CHAMBOURNIER, Gilles;PAMMENT, Michael, G.;FEDIJ, Victor WO2017/86941, 2017, A1

1253955-17-7 Synthesis