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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 879827Generated: October 30, 2026

(3S,8S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid → TT-OAD2 (free base)

https://huagongshe.com/reaction/879827

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(3S,8S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acidHCID 58327369—
ReactantL-Phenylalanine, 4-(2,3-dimethyl-4-pyridinyl)-, methyl ester, hydrochloride (1:2)HCID 66719267—
ProductTT-OAD2 (free base)HCID 58327143—

Reaction Steps

The title compound (110 mg) was prepared from (3S,8S)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid and (S)-2-amino-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester dihydrochloride according to General Procedures L and B. LCMS (m/z): 857. 1H NMR (400 MHz, acetone-d6): 8.18(d, 1H), 7.86(d, 1H), 7.59(d, 1H), 7.49(d, 1H), 7.36(dd, 1H), 7.23-7.18(m, 4H), 7.15(m, 1H), 7.11-7.07(m, 4H), 6.86(d, 1H), 6.78-6.72(m, 4H), 6.61(s, 1H), 6.52(s, 1H), 5.03(s, 2H), 4.93(dd, 1H), 4.72(m, 1H), 4.14(dd, 1H), 3.67(dd, 1H), 3.54(dd, 1H), 3.45(d, 1H), 3.39(dd, 1H), 3.23(d, 1H), 3.03(dd, 1H), 2.89-2.79(m, 2H), 2.66(dd, 1H), 2.38(s, 3H), 2.02(s, 3H), 1.87-1.75(m, 1H), 1.72-1.61(m, 1H), 0.48(t, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08987295B2
Source datasetuspto-grants-2015_03
ORD IDord-cec3d26c3d744464bd56a0b32caae11d
Source noteuspto-grants-2015_03