2-Amino-3-(1-trityl-1h-imidazol-4-yl)-2-(1-trityl-1h-imidazol-4-ylmethyl)-propionic acid methyl ester → 3-(3-Benzenesulfonyl-3-aza-bicyclo[3.1.0]hex-6-yl)-2-thioxo-5,5-bis-(1-trityl-1H-imidazol-4-ylmethyl)-imidazolidin 4one

HRID 636814Notes

Reaction equation

HRID 636814 reaction equation
C[O:2][C:3](=O)[C:4]([NH2:55])([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.[C:57]1([S:63]([N:66]2[CH2:71][CH:70]3[CH:68]([CH:69]3[N:72]=[C:73]=[S:74])[CH2:67]2)(=[O:65])=[O:64])[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>>[C:57]1([S:63]([N:66]2[CH2:71][CH:70]3[CH:68]([CH:69]3[N:72]3[C:3](=[O:2])[C:4]([CH2:5][C:6]4[N:7]=[CH:8][N:9]([C:11]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)([C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=5)[CH:10]=4)([CH2:30][C:31]4[N:32]=[CH:33][N:34]([C:36]([C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)([C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)[C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)[CH:35]=4)[NH:55][C:73]3=[S:74])[CH2:67]2)(=[O:65])=[O:64])[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

Participants

3

Reactant 2

HCID 154914332-Amino-3-(1-trityl-1h-imidazol-4-yl)-2-(1-trityl-1h-imidazol-4-ylmethyl)-propionic acid methyl esterHCID 212553093-Benzenesulfonyl-6-isothiocyanato-3-aza-bicyclo[3.1.0]hexane

Product 1

HCID 882180533-(3-Benzenesulfonyl-3-aza-bicyclo[3.1.0]hex-6-yl)-2-thioxo-5,5-bis-(1-trityl-1H-imidazol-4-ylmethyl)-imidazolidin 4one

Procedure

Using the same procedure as described in Example 1B, the reaction mixture of the title compound of 53B (0.68 mmol) and 3-benzenesulfonyl-6-isothiocyanato-3-aza-bicyclo[3.1.0]hexane (6.71 mmol, prepared in 1A) was heated to reflux overnight under an atmosphere of dry N2. It was then poured into 10% K2CO3 aqueous solution and extracted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4 and concentrated to afford the crude product. The crude product was chromatographed on silica gel with MeOH—CHCl3—NH4OH (1:99:0.1) as eluents to afford the title compound of 56B as a yellow solid, 0.548 g (0.558 mmol, 82% yield).

Sources & evidence

ORD record
ord-d4b34b7d53c245d28ad728e7e0910486
Source dataset
uspto-grants-2001_02
Patent number
US06194438B1

Reaction notes

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