(S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate → (S)-Tert-butyl 2-(5-(4'-(2-((S)-7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonan-8-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 71971Notes

Reaction equation

COC(=O)N[C@@H](C(C)C)C(N1[C@H](C2NC(C3C=CC4C(=CC=C([C:30]5[CH:35]=[CH:34][C:33]([C:36]6[NH:40][C:39]([C@@H:41]7[CH2:49][C:44]8([O:48][CH2:47][CH2:46][O:45]8)[CH2:43][N:42]7[C:50](=[O:60])[C@@H:51]([NH:55][C:56]([O:58][CH3:59])=[O:57])[CH:52]([CH3:54])[CH3:53])=[N:38][CH:37]=6)=[CH:32][CH:31]=5)C=4)C=3)=CN=2)CC2(CC2)C1)=O.BrC1C=C2C(=CC=1)C=C(C1NC([C@@H]3CC4(CC4)CN3C(=O)[C@@H](NC(=O)OC)C(C)C)=NC=1)C=C2.BrC1C=CC(C2NC([C@@H]3CC4(OCCO4)CN3C(=O)[C@@H](NC(=O)OC)C(C)C)=NC=2)=CC=1.Br[C:132]1[CH:137]=[CH:136][C:135]([C:138]2[NH:142][C:141]([C@@H:143]3[CH2:147][CH2:146][CH2:145][N:144]3[C:148]([O:150][C:151]([CH3:154])([CH3:153])[CH3:152])=[O:149])=[N:140][CH:139]=2)=[CH:134][CH:133]=1>>[CH3:59][O:58][C:56]([NH:55][C@@H:51]([CH:52]([CH3:53])[CH3:54])[C:50]([N:42]1[C@H:41]([C:39]2[NH:40][C:36]([C:33]3[CH:32]=[CH:31][C:30]([C:132]4[CH:133]=[CH:134][C:135]([C:138]5[NH:142][C:141]([C@@H:143]6[CH2:147][CH2:146][CH2:145][N:144]6[C:148]([O:150][C:151]([CH3:154])([CH3:153])[CH3:152])=[O:149])=[N:140][CH:139]=5)=[CH:136][CH:137]=4)=[CH:35][CH:34]=3)=[CH:37][N:38]=2)[CH2:49][C:44]2([O:48][CH2:47][CH2:46][O:45]2)[CH2:43]1)=[O:60])=[O:57]

Participants

Reactant 4

HCID 56605031(S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HCID 59610362((S)-1-{(S)-8-[4-(4-Bromo-phenyl)-1H-imidazol-2-yl]-1,4-dioxa-7-aza-spiro[4.4]nonane-7-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester2×

HCID 59610451(S)-1-((S)-6-(5-(6-(4-(2-((S)-7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonan-8-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-1H-imidazol-2-yl)-5-azaspiro[2.4]heptan-5-yl)-3-methyl-1-oxobutan-2-yl-carbamic acid methyl ester

HCID 59610490methyl(S)-1-((S)-6-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)-5-azaspiro[2.4]heptan-5-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Product 1

HCID 59610597(S)-Tert-butyl 2-(5-(4'-(2-((S)-7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonan-8-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Procedure

Title compound was prepared according to the method employed to prepare (S)-1-((S)-6-(5-(6-(4-(2-((S)-7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonan-8-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-1H-imidazol-2-yl)-5-azaspiro[2.4]heptan-5-yl)-3-methyl-1-oxobutan-2-yl-carbamic acid methyl ester, except instead of methyl (S)-1-((S)-6-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)-5-azaspiro[2.4]heptan-5-yl)-3-methyl-1-oxobutan-2-ylcarbamate and methyl (S)-1-((S)-8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamate, methyl (S)-1-((S)-8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamate (600 mg, 1.182 mmol) and (S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (510 mg, 1.3 mmol). The amount for all the other reagents were adjusted accordingly. 489 mg (56%).

Sources & evidence

ORD record: ord-10f60035409c40c69a9dd2974fbe2a47
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822430B2

Reaction notes

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