2-Oxo-4-phenylbutyric acid → HCID 18605782, compound

HRID 2118880Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[C:3]1=[O:21].O=[C:23]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:24]([OH:26])=[O:25].C([BH3-])#N.[Na+]>>[C:18]([CH:9]([N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:2]([NH:1][CH:23]([C:24]([OH:26])=[O:25])[CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:3]1=[O:21])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([OH:20])=[O:19]

Participants

Reactant 3

HCID 697322-Oxo-4-phenylbutyric acid

HCID 5003444Sodium cyanoborohydride

HCID 18605805HCID 18605805, compound

Product 1

HCID 18605782HCID 18605782, compound

Procedure

Methyl 3-(p-phydroxyphenyl)-2-oxopropionate and α-t-Boc-L-lysine are condensed in the presence of sodium cyanoborohydride as described in Example 19. Subsequent ring closure, saponification of methyl ester, and removal of the t-butoxycarbonyl group with formic acid gives 3-(S)-amino-1-[1-carboxy-2-(4-hydroxyphenyl)ethyl]perhydroazepin-2-one. The caprolactam and 2-oxo-4-phenylbutyric acid are condensed in the presence of sodium cyanoborohydride to yield 1-[1-carboxy-2-(4-hydroxyphenyl)ethyl]-3-(S)-[(1-carboxy-3-phenylpropyl)amino]perhydroazepin-2-one.

Sources & evidence

ORD record: ord-86c5e7e54be04ebe8538217dc36f9ce4
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04680392

Reaction notes

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