(R)-3-((tert-butoxycarbonyl)amino)-4-(naphthalen-2-yl)butanoic acid → (R)-3-amino-1((R)-3-(5,6-dichloro-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-(naphthalen-2-yl)butan-1-one

HRID 1096601Notes

Reaction equation

C(OC([NH:8][C@H:9]([CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)[CH2:10][C:11]([OH:13])=O)=O)(C)(C)C.[Cl:25][C:26]1[C:45]([Cl:46])=[CH:44][C:29]2[N:30]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:31]([C@@H:33]3[CH2:38][CH2:37][CH2:36][NH:35][CH2:34]3)=[N:32][C:28]=2[CH:27]=1>>[NH2:8][C@H:9]([CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)[CH2:10][C:11]([N:35]1[CH2:36][CH2:37][CH2:38][C@@H:33]([C:31]2[N:30]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:29]3[CH:44]=[C:45]([Cl:46])[C:26]([Cl:25])=[CH:27][C:28]=3[N:32]=2)[CH2:34]1)=[O:13]

Participants

Reactant 2

HCID 7021578(R)-3-((tert-butoxycarbonyl)amino)-4-(naphthalen-2-yl)butanoic acid

HCID 66785803(R)-5,6-dichloro-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole

Product 1

HCID 66785734(R)-3-amino-1((R)-3-(5,6-dichloro-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-(naphthalen-2-yl)butan-1-one

Procedure

The title compound was prepared according to the procedure outlined in Example DI, Steps A-F, using reagents (R)-3-(tert-butoxycarbonylamino)-4-(naphthalen-2-yl)butanoic acid and (R)-5,6-dichloro-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole in Step E. ESI-MS: m/z 553.4 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35-1.52 (m, 1H) 1.65-1.89 (m, 3H) 1.91-2.10 (m, 2H) 2.60-2.82 (m, 2H) 2.89-3.18 (m, 7H) 3.18-3.44 (m, 3H) 3.69-3.99 (m, 2H) 4.07-4.21 (m, 1H) 4.23-4.53 (m, 2H) 7.40-7.57 (m, 3H) 7.75-8.00 (m, 6H).

Sources & evidence

ORD record: ord-fd65090aaaec429ca0ae2bcf1964f97d
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138168B1

Reaction notes

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