(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)

HRID 879827Notes

Reaction equation

HRID 879827 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:38][O:37][C:16]3=[CH:17][C:18]4[CH2:19][C@@H:20]([C:34](O)=[O:35])[N:21]([C@H:25]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH2:26][CH3:27])[CH2:22][C:23]=4[CH:24]=[C:15]3[O:14]2)=[CH:9][CH:8]=1.Cl.Cl.C[O:46][C:47](=[O:65])[C@@H:48]([NH2:64])[CH2:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][N:59]=[C:58]([CH3:62])[C:57]=2[CH3:63])=[CH:52][CH:51]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]2[CH2:38][O:37][C:16]3=[CH:17][C:18]4[CH2:19][C@@H:20]([C:34]([NH:64][C@@H:48]([CH2:49][C:50]5[CH:55]=[CH:54][C:53]([C:56]6[CH:61]=[CH:60][N:59]=[C:58]([CH3:62])[C:57]=6[CH3:63])=[CH:52][CH:51]=5)[C:47]([OH:46])=[O:65])=[O:35])[N:21]([C@H:25]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH2:26][CH3:27])[CH2:22][C:23]=4[CH:24]=[C:15]3[O:14]2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 58327369(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 66719267L-Phenylalanine, 4-(2,3-dimethyl-4-pyridinyl)-, methyl ester, hydrochloride (1:2)

Product 1

HCID 58327143TT-OAD2 (free base)

Procedure

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).

Sources & evidence

ORD record
ord-cec3d26c3d744464bd56a0b32caae11d
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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