1,2,3,4-Tetrahydroisoquinoline → (3Ez,5s)-5-(3,4-dihydro-2(1h)-isoquinolinylcarbonyl)-1-[(2',3-dimethyl[1,1'-biphenyl]-4-yl)carbonyl]-3-pyrrolidinone o-methyloxime

HRID 1349322Notes

Reaction equation

HRID 1349322 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16]([OH:18])=O)=[O:7])(C)(C)C.[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][C:29](C(O)=O)=[C:28]([CH3:35])[CH:27]=1.[CH2:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][NH:37]1>>[CH3:15][O:14][N:13]=[C:11]1[CH2:10][C@@H:9]([C:16]([N:37]2[CH2:38][CH2:39][C:40]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:36]2)=[O:18])[N:8]([C:6]([C:29]2[CH:30]=[CH:31][C:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH3:19])=[CH:27][C:28]=2[CH3:35])=[O:7])[CH2:12]1

Participants

4

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 219372462',3-Dimethyl[1,1'-biphenyl]-4-carboxylic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725654(3Ez,5s)-5-(3,4-dihydro-2(1h)-isoquinolinylcarbonyl)-1-[(2',3-dimethyl[1,1'-biphenyl]-4-yl)carbonyl]-3-pyrrolidinone o-methyloxime

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 2′,3-dimethyl[1,1′-biphenyl]-4-carboxylic acid, and 1,2,3,4-tetrahydroisoquinoline, the title compound was obtained in 77% purity by HPLC. MS(ESI+): m/z=482.

Sources & evidence

ORD record
ord-cd0e0ce3b52447e8b4faefc70c572f80
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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