3-Amino-3-Oxopropanoic Acid → (3aR,4S,7aR)-methyl 4-(3-amino-3-oxopropanoyloxy)-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate

HRID 2176781Notes

Reaction equation

HRID 2176781 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].[NH2:24][C:25](=[O:30])[CH2:26][C:27](O)=[O:28]>>[NH2:24][C:25](=[O:30])[CH2:26][C:27]([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:28]

Participants

3

Reactant 2

HCID 753673-Amino-3-Oxopropanoic AcidHCID 68276168(3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

Product 1

HCID 60142969(3aR,4S,7aR)-methyl 4-(3-amino-3-oxopropanoyloxy)-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 3-amino-3-oxopropanoic acid to yield (3aR,4S,7aR)-methyl 4-(3-amino-3-oxopropanoyloxy)-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate. MS [M+H]=296 (ester elimination ion); RT=0.96 min; UPLC Method I

Sources & evidence

ORD record
ord-b1c794b8d2714a25ae0152902c08d774
Source dataset
uspto-grants-2015_06
Patent number
US09067881B2

Reaction notes

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