Benzoyl chloride → (S)-2-({(3S,8S)-7-Benzoyl-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2-methyl-pyridin-4-yloxy)-phenyl]-propionic acid

HRID 879824Notes

Reaction equation

HRID 879824 reaction equation
CO[C:3](=[O:40])[C@@H:4]([NH:32][C:33](OC(C)(C)C)=O)[CH2:5][C:6]1[CH:31]=[CH:30][C:9]2[O:10][C@@H:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=4)=[CH:16][CH:15]=3)[CH2:12][O:13][C:8]=2[CH:7]=1.[C:41](Cl)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.Cl.Cl.C[O:53][C:54](=[O:72])[C@@H:55]([NH2:71])[CH2:56][C:57]1[CH:62]=[CH:61][C:60]([O:63][C:64]2[CH:69]=[CH:68][N:67]=[C:66]([CH3:70])[CH:65]=2)=[CH:59][CH:58]=1>>[C:41]([N:32]1[C@H:4]([C:3]([NH:71][C@@H:55]([CH2:56][C:57]2[CH:62]=[CH:61][C:60]([O:63][C:64]3[CH:69]=[CH:68][N:67]=[C:66]([CH3:70])[CH:65]=3)=[CH:59][CH:58]=2)[C:54]([OH:53])=[O:72])=[O:40])[CH2:5][C:6]2[CH:7]=[C:8]3[O:13][CH2:12][C@H:11]([C:14]4[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]5[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=5)=[CH:18][CH:19]=4)[O:10][C:9]3=[CH:30][C:31]=2[CH2:33]1)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 58327295(S)-2-tert-Butoxycarbonylamino-3-{(S)-2-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3-dihydro-benzo[1,4]dioxin-6-yl}-propionic acid methyl esterHCID 66719770(s)-2-Amino-3-[4-(2-methyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester dihydrochloride

Product 1

HCID 58327456(S)-2-({(3S,8S)-7-Benzoyl-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2-methyl-pyridin-4-yloxy)-phenyl]-propionic acid

Procedure

The title compound (24 mg) was prepared from (S)-2-tert-butoxycarbonylamino-3-{(S)-2-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3-dihydro-benzo[1,4]dioxin-6-yl}-propionic acid methyl ester, which was deprotected according to General Procedure C, subjected to General Procedure V, then acylated with benzoyl chloride according to General Procedure F. Hydrolysis followed General Procedure B and the resulting acid and (S)-2-amino-3-[4-(2-methyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester dihydrochloride were reacted according to General Procedures L and B. LCMS (m/z): 845.

Workup

  1. customHydrolysis

Sources & evidence

ORD record
ord-24573138efe1431a80d20886419c6b3a
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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