4-(Dipropylcarbamoyl)butanoic acid → (3aR,4S,7aR)-methyl 4-(5-(dipropylamino)-5-oxopentanoyloxy)-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate

HRID 2176794Notes

Reaction equation

HRID 2176794 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].[CH2:24]([N:27]([CH2:36][CH2:37][CH3:38])[C:28]([CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])=[O:29])[CH2:25][CH3:26]>>[CH2:36]([N:27]([CH2:24][CH2:25][CH3:26])[C:28](=[O:29])[CH2:30][CH2:31][CH2:32][C:33]([O:23][C@@:9]1([C:14]#[C:15][C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:11][CH2:12][C@@H:13]2[C@H:8]1[CH2:7][CH2:6][N:5]2[C:3]([O:2][CH3:1])=[O:4])=[O:34])[CH2:37][CH3:38]

Participants

3

Reactant 2

HCID 167729014-(Dipropylcarbamoyl)butanoic acidHCID 68276168(3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

Product 1

HCID 60141047(3aR,4S,7aR)-methyl 4-(5-(dipropylamino)-5-oxopentanoyloxy)-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate

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 4-dipropylcarbamoyl-butyric acid to yield (3aR,4S,7aR)-methyl 4-(5-(dipropylamino)-5-oxopentanoyloxy)-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate. MS [2M+H+NH4]=1039; RT=1.41 min; UPLC Method I

Sources & evidence

ORD record
ord-6e6596db2b384b368dec7bdcf0d6d97c
Source dataset
uspto-grants-2015_06
Patent number
US09067881B2

Reaction notes

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