Methyl isonipecotate → HCID 22602748, compound

HRID 2085063Notes

Reaction equation

FC(F)(F)C(O)=O.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[C:22]([S:26](N[C@H](C#C)CC(O)=O)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1.[NH:37]1[CH2:46][CH2:45][CH:40]([C:41]([O:43]C)=[O:42])[CH2:39][CH2:38]1>>[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[C:22]([S:26]([N:37]2[CH2:46][CH2:45][CH:40]([C:41]([OH:43])=[O:42])[CH2:39][CH2:38]2)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1

Participants

Reactant 2

HCID 424914Methyl isonipecotate

HCID 86759416HCID 86759416, compound

Product 1

HCID 22602748HCID 22602748, compound

Procedure

The procedure for the preparation of the product of EXAMPLE 17 was repeated using methyl isonipecotate (Aldrich) in the place of ethyl (3S)-3-aminopent-4-ynoate hydrochloride to provide the title product. 1H (CD3OD): δ 7.86 (1H, d); 7.61 (1H, t); 7.49 (1H, t); 7.32 (1H, d); 7.24 (1H, s); 7.20 (1H, d); 6.74 (1H, d); 6.66 (1H, t); 4.12 (2H, t); 3.57 (2H, br. d); 3.37 (2H, t); 2.52 (2H, t); 2.27 (1H, tt); 1.94 (4H, m); 1.84 (2H, p); 1.71 (2H, br. q).

Sources & evidence

ORD record: ord-f4a7f85c16aa46bbb1560085dc71bc46
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06720315B2

Reaction notes

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