(2S)-2-(((tert-butoxy)carbonyl)amino)hex-5-enoic acid → (S,Z)-3-amino-1-phenyl-1,4,5,8-tetrahydroazocin-2(3H)-one

Reaction equation

F[C:2](F)(F)C(O)=O.[NH2:8][C@H:9]1[CH2:15][CH:14]=[CH:13][CH2:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]1=[O:22].C(OC(N[C@@H](CCC=C)C(O)=O)=O)(C)(C)C>>[NH2:8][C@H:9]1[CH2:15][CH2:14][CH:13]=[CH:12][CH2:2][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]1=[O:22]

Participants

Reactant 2

HCID 20765220(2S)-2-(((tert-butoxy)carbonyl)amino)hex-5-enoic acid

HCID 68292369(S,Z)-3-Amino-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-one trifluoroacetate

Product 1

HCID 68292461(S,Z)-3-amino-1-phenyl-1,4,5,8-tetrahydroazocin-2(3H)-one

Procedure

(S,Z)-3-Amino-1-phenyl-1,4,5,8-tetrahydroazocin-2 (3H)-one (175 mg, 0.692 mmol) was synthesized as described for the preparation of Intermediate 52 using (S)-2-(tert-butoxycarbonylamino)hex-5-enoic acid in step A. Anal. Calcd. for C13H16N2O m/z 216.2. found: 217.0 (M+H)+.

Sources & evidence

ORD record: ord-28cb62f94f9a4ae99b34551111226402
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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