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

HRID 529017Notes

Reaction equation

HRID 529017 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([C:16](=[O:26])[N:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[N:13]=[C:12]1[C:27]1[CH:35]=[CH:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[CH:32][C:28]=1[C:29](O)=[O:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si:40]([O:47][CH2:48][C@@H:49]1[CH2:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH2:51][NH:50]1)([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]>>[Si:1]([O:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([C:16](=[O:26])[N:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[N:13]=[C:12]1[C:27]1[CH:35]=[CH:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[CH:32][C:28]=1[C:29]([N:50]1[C@H:49]([CH2:48][O:47][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:41])[CH3:42])[CH2:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH2:51]1)=[O:30])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 10333747(S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinolineHCID 710624512-(1-(2-(tert-Butyldimethylsilyloxy)ethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 86718935Methyl 4-(1-(2-(tert-butyldimethylsilyloxy)ethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-3-((S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoateYield 87%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 271H, 2-(1-(2-(tert-butyldimethylsilyloxy)ethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acid (105 mg, 0.19 mmol) and (S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline (62 mg, 0.22 mmol) were converted to the title compound (133 mg, 87%). MS(ESI+) m/z 820.2 (M+H)+.

Sources & evidence

ORD record
ord-610fa303a773445798d0936d0ac63742
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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