(S)-2,2-Dimethyl-3-(3-oxohexahydroimidazo[1,5-a]pyrazin-2(3H)-yl)propanoic acid → (1S,2R)-2-[(8aS)-3-oxo-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyrazin-2-yl]cyclopentanecarboxylic acid

HRID 590568Notes

Reaction equation

HRID 590568 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C@H:5]2[CH2:4][N:3]1[CH2:11][C:12]([CH3:17])(C)[C:13]([OH:15])=[O:14].F[C:19](F)(F)[C:20](O)=O.N[C@@H]1CCC[C@@H]1C(OCC)=O>>[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C@H:5]2[CH2:4][N:3]1[C@@H:11]1[CH2:20][CH2:19][CH2:17][C@@H:12]1[C:13]([OH:15])=[O:14]

Participants

3

Reactant 2

HCID 118354187(S)-2,2-Dimethyl-3-(3-oxohexahydroimidazo[1,5-a]pyrazin-2(3H)-yl)propanoic acidHCID 131734488ethyl (1S,2R)-2-aminocyclopentanecarboxylate trifluoroacetic acid salt2×

Product 1

HCID 118354515(1S,2R)-2-[(8aS)-3-oxo-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyrazin-2-yl]cyclopentanecarboxylic acid

Procedure

Compound 50-A was prepared in analogy to compound Q in Example 19 by using ethyl (1S,2R)-2-aminocyclopentanecarboxylate trifluoroacetic acid salt (compound 50-B) instead of ethyl 3-amino-2,2-dimethyl-propanoate hydrochloride salt.

Sources & evidence

ORD record
ord-680fddc0a26d416986cfaf94feaead95
Source dataset
uspto-grants-2016_01
Patent number
US09233978B2

Reaction notes

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