Ethanol → HCID 70446296, compound

HRID 2118878Notes

Reaction equation

C(OC([NH:8][C@H:9]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH:16](C(O)=O)C)[C:10]1=[O:21])=O)(C)(C)C.S(Cl)([Cl:24])=[O:23].[CH2:26]([OH:28])[CH3:27]>>[ClH:24].[NH2:8][C@H:9]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([C:16]([O:28][CH2:26][CH3:27])=[O:23])[C:10]1=[O:21]

Participants

Reactant 3

HCID 702Ethanol

HCID 24386Thionyl Chloride

HCID 13749515HCID 13749515, compound

Product 1

HCID 70446296HCID 70446296, compound

Procedure

3-(S)-t-Butoxycarbonylamino-1-(1-carboxyethyl)perhydroazepin-2-one (Isomer A) (2 g), prepared as in Example 12, was treated with thionyl chloride in absolute ethyl alcohol to provide 2.07 g of the 3-(S)-amino-1-(1-ethoxycarbonyl)perhydroazepin-2-one hydrochloride. This material, following careful neutralization with ethanolic sodium ethoxide, was condensed with benzyl 2-keto-4-phenylbutyrate in the same manner as Example 1, the keto ester having been prepared by thionyl chloride treatment of the ketoacid in benzyl alcohol and purified via the sodium bisulfite addition product. The diastereoisomeric mixture resulting from the reductive amination (10.6 g) was chromatographed over silica gel to yield the individual isomers:

Sources & evidence

ORD record: ord-4508aea0267f428b83f294c2a90a82f8
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04680392

Reaction notes

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