2-(Benzylidene-amino)-3-(1-trityl-1H-imidazol-4-yl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-propionic acid methyl ester → 2-Amino-3-(1-trityl-1h-imidazol-4-yl)-2-(1-trityl-1h-imidazol-4-ylmethyl)-propionic acid methyl ester

HRID 636813Notes

Reaction equation

HRID 636813 reaction equation
[CH3:1][O:2][C:3](=[O:63])[C:4]([N:55]=CC1C=CC=CC=1)([CH2:30][C:31]1[N:32]=[CH:33][N:34]([C:36]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=1)[CH2:5][C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1>C1COCC1>[CH3:1][O:2][C:3](=[O:63])[C:4]([NH2:55])([CH2:5][C:6]1[N:7]=[CH:8][N:9]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:10]=1)[CH2:30][C:31]1[N:32]=[CH:33][N:34]([C:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:35]=1

Participants

3

Reactant 1

HCID 154914322-(Benzylidene-amino)-3-(1-trityl-1H-imidazol-4-yl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-propionic acid methyl ester

Product 1

HCID 154914332-Amino-3-(1-trityl-1h-imidazol-4-yl)-2-(1-trityl-1h-imidazol-4-ylmethyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude title compound of 53A was dissolved in anhydrous THF (40 ml). To the reaction was added 10 ml of a solution of 2.0 M aqueous hydrochloric acid (HCl) at 0° C. The mixture was stirred at ambient temperature for two hours. The reaction was subsequently concentrated under vacuum to remove the THF. The reaction was then partitioned between ethyl ether and water. The aqueous layer was washed two more times with ethyl ether. The pH of the aqueous layer was then adjusted to 9 with sodium carbonate (Na2CO3) and the solution is extracted with methylene chloride until virtually no product is left in the methylene chloride (CH2Cl2) layer. The CH2Cl2 extracts were combined, dried over MgSO4, filtered and concentrated under vacuum to give the crude product. The crude product was chromatographed on silica gel with MeOH—CHCl3—NH40H (1:99:0.1) as eluents to afford the title compound of 56B as a white foam, 10.78 g (14.7 mmol, 68% yield for two steps).

Sources & evidence

ORD record
ord-0a8e6286ecb74f5ca180baa85fd32009
Source dataset
uspto-grants-2001_02
Patent number
US06194438B1

Reaction notes

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