2-Methyl-3-pentanone → (s)-2-{[(3s,8s)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-7-(1-ethyl-2-methyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid

HRID 391934Notes

Reaction equation

HRID 391934 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)=[C:24](Cl)[CH:23]=4)=[CH:16][CH:15]=3)[CH2:12][O:13][C:8]=2[CH:7]=1.[CH3:41][CH:42]([C:44](=O)[CH2:45][CH3:46])[CH3:43].[ClH:48].[ClH:49].C[O:51][C:52](=[O:70])[C@@H:53]([NH2:69])[CH2:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[CH:66]=[CH:65][N:64]=[C:63]([CH3:67])[C:62]=2[CH3:68])=[CH:57][CH:56]=1>>[Cl:48][C:26]1[CH:27]=[C:22]([CH:23]=[CH:24][C:25]=1[Cl:49])[CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:11]2[CH2:12][O:13][C:8]3=[CH:7][C:6]4[CH2:5][C@@H:4]([C:3]([NH:69][C@@H:53]([CH2:54][C:55]5[CH:60]=[CH:59][C:58]([C:61]6[CH:66]=[CH:65][N:64]=[C:63]([CH3:67])[C:62]=6[CH3:68])=[CH:57][CH:56]=5)[C:52]([OH:51])=[O:70])=[O:40])[N:32]([CH:44]([CH2:45][CH3:46])[CH:42]([CH3:43])[CH3:41])[CH2:33][C:31]=4[CH:30]=[C:9]3[O:10]2)=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 112652-Methyl-3-pentanoneHCID 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 66719267L-Phenylalanine, 4-(2,3-dimethyl-4-pyridinyl)-, methyl ester, hydrochloride (1:2)

Product 1

HCID 58327219(s)-2-{[(3s,8s)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-7-(1-ethyl-2-methyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid

Procedure

The title compound (15 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, then treated with 2-methyl-3-pentanone according to General Procedure M. The reductive amination product was subjected to General Procedures V and B in succession, then the resulting acid and (S)-2-amino-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester dihydrochloride were reacted according to General Procedures L and B. LCMS (m/z): 823.

Sources & evidence

ORD record
ord-2a57ba20041e405e9243fcc01fd60699
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

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