N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → HCID 68276317, compound

HRID 2176762Notes

Reaction equation

HRID 2176762 reaction equation
[CH3:1][O:2][C:3]([N:5]1[C@@H:13]2[C@@H:8]([C@@:9]([OH:23])([C:14]#[C:15][C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[C:24]([O:28][C:29]([NH:31][CH2:32][CH2:33][C:34](O)=[O:35])=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[CH3:1][O:2][C:3]([N:5]1[C@H:13]2[C@H:8]([C@:9]([O:23][C:34](=[O:35])[CH2:33][CH2:32][NH:31][C:29]([O:28][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:30])([C:14]#[C:15][C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 68276168(3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

Product 1

HCID 68276317HCID 68276317, compound

Procedure

Synthesis in analogy to the General Method 1 starting from (3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester and 3-tert-butoxycarbonylamino-propionic acid to yield (3aR,4S,7aR)-4-(3-tert-butoxycarbonylamino-propionyloxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester. This NBoc-protected product was then stirred in hydrochloric acid dioxane solution (4M, 10 equiv.) at room temperature for 6 hrs. Subsequently the solvent was removed the residue dissolved in dichloromethane and washed with saturated sodium hydrogencarbonate solution. The organic layer was tried with sodium sulfate, filtrated and evaporated. The crude product was subjected to silica gel flash chromatography (ISCO CombiFlash; dichloromethane/methanol; 100/0 to 95/5) to yield (3aR,4S,7aR)-methyl 4-(3-aminopropanoyloxy)-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate. MS [M+Na]=407; RT=4.395 min; LC-MS Method II

Sources & evidence

ORD record
ord-056990f0c68248de90fe219be0fa379d
Source dataset
uspto-grants-2015_06
Patent number
US09067881B2

Reaction notes

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