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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1696293Generated: October 25, 2026

(2R,3S)-3-amino-1-((S)-6-ethylchroman-4-ylamino)-4-phenylbutan-2-ol → N-((2S,3R)-4-((S)-6-Ethylchroman-4-ylamino)-3-hydroxy-1-phenylbutan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamide

https://huagongshe.com/reaction/1696293

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2R,3S)-3-amino-1-((S)-6-ethylchroman-4-ylamino)-4-phenylbutan-2-olHCID 66844744—
ReactantLithium benzomorpholine-2-carboxylateHCID 69210254—
ProductN-((2S,3R)-4-((S)-6-Ethylchroman-4-ylamino)-3-hydroxy-1-phenylbutan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamideHCID 66844673—

Reaction Steps

The title compound was prepared using a procedure analogous to that described in Example 35, wherein (±)-lithium 3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate was coupled with (2R,3S)-3-amino-1-((S)-6-ethylchroman-4-ylamino)-4-phenylbutan-2-ol to afford the title compound (a 1:1 mixture of epimers at the benzooxazine stereocenter) as a white solid. MS m/z: 502 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163766B2
Source datasetuspto-grants-2012_04
ORD IDord-9bca0a0d289e4c7796a23c5fda93275f
Source noteuspto-grants-2012_04