1-Hydroxy-1-cyclopropanecarboxylic acid → 8-(1-Hydroxy-cyclopropanecarbonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194197Notes

Reaction equation

HRID 2194197 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(O)(=O)C.[F:27][C:28]([F:48])([F:47])[O:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:40][CH2:39][C:38]3([CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[C:37]2=[O:46])=[CH:32][CH:31]=1.[OH:49][C:50]1([C:53](O)=[O:54])[CH2:52][CH2:51]1>>[OH:49][C:50]1([C:53]([N:43]2[CH2:42][CH2:41][C:38]3([C:37](=[O:46])[N:36]([C:33]4[CH:34]=[CH:35][C:30]([O:29][C:28]([F:27])([F:47])[F:48])=[CH:31][CH:32]=4)[CH2:40][CH2:39]3)[CH2:45][CH2:44]2)=[O:54])[CH2:52][CH2:51]1

Participants

4

Reactant 3

HCID 27331601-Hydroxy-1-cyclopropanecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667873332-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one acetic acid salt

Product 1

HCID 595779318-(1-Hydroxy-cyclopropanecarbonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

Procedure

The title compound was prepared in analogy to example 13 step A (using TBTU instead of BOP as the coupling reagent) from 2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one acetic acid salt (described in example 180 step C) and 1-hydroxy-cyclopropanecarboxylic acid. White solid. MS (ESI): 399.1 (MH+).

Sources & evidence

ORD record
ord-b1daf03b7cff4373a1e30d30b2d69ec7
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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