Trifluoroacetic acid → 2-{[1-(4-Chloro-phenyl)-2-cyclopropyl-2,7-diaza-spiro[3.5]nonane-7-carbonyl]-amino}-3-methyl-pentanoic acid methyl ester

HRID 1869228Notes

Reaction equation

HRID 1869228 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:11]3([CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[CH2:10][N:9]2[CH:24]2[CH2:26][CH2:25]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.[N:34]([C@@H:37]([C@@H:42]([CH3:45])[CH2:43][CH3:44])[C:38]([O:40][CH3:41])=[O:39])=[C:35]=[O:36]>>[CH3:41][O:40][C:38](=[O:39])[CH:37]([NH:34][C:35]([N:14]1[CH2:15][CH2:16][C:11]2([CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]([CH:24]3[CH2:26][CH2:25]3)[CH2:10]2)[CH2:12][CH2:13]1)=[O:36])[CH:42]([CH3:45])[CH2:43][CH3:44]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7019165(2S,3S)-2-Isocyanato-3-methylvaleric Acid Methyl EsterHCID 579860421,1-Dimethylethyl 1-(4-chlorophenyl)-2-cyclopropyl-2,7-diazaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 688657332-{[1-(4-Chloro-phenyl)-2-cyclopropyl-2,7-diaza-spiro[3.5]nonane-7-carbonyl]-amino}-3-methyl-pentanoic acid methyl ester

Procedure

Treat the compound from Example 2 with TFA according to the procedure of step D in Example 1 and treat the resultant product from this reaction with (2S,3S)-2-isocyanato-3-methylvaleric acid, methyl ester according to the procedure Example 1 step E to give the title compound which is characterized by LCMS. (MWT 448).

Sources & evidence

ORD record
ord-1d2e12d051a04b87bf29ae32721e8d41
Source dataset
uspto-grants-2009_12
Patent number
US07638526B2

Reaction notes

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