(S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline → Methyl 3-((S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)benzoate

HRID 529029Notes

Reaction equation

HRID 529029 reaction equation
[CH2:1]([N:5]([CH2:27][CH2:28][CH2:29][CH3:30])[C:6]([C:8]1[N:9]=[C:10]([C:14]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][C:15]=2[C:16]([OH:18])=O)[N:11]([CH3:13])[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[Si:31]([O:38][CH2:39][C@@H:40]1[CH2:49][C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:42][NH:41]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>>[Si:31]([O:38][CH2:39][C@@H:40]1[CH2:49][C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:42][N:41]1[C:16]([C:15]1[CH:19]=[C:20]([CH:21]=[CH:22][C:14]=1[C:10]1[N:11]([CH3:13])[CH:12]=[C:8]([C:6](=[O:7])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:27][CH2:28][CH2:29][CH3:30])[N:9]=1)[C:23]([O:25][CH3:26])=[O:24])=[O:18])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

3

Reactant 2

HCID 10333747(S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinolineHCID 710622052-(4-(Dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acid2×

Product 1

HCID 86718947Methyl 3-((S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)benzoateYield 87.5%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 271H, 2-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acid (Intermediate 281B, 170 mg, 0.42 mmol) and (S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline (237 mg, 0.85 mmol) were converted to the title compound (248 mg, 87%). MS(ESI+) m/z 675 (M+H)+.

Sources & evidence

ORD record
ord-0c08b8dde698401fa6749677008400e4
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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