Triethylamine → (S)-1-[2-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-sulfonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

HRID 25321Notes

Reaction equation

HRID 25321 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:13][C:14]1[CH:15]=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[NH:28][C:29]4[CH:39]=[CH:38][C:37]5[C:32](=[C:33]([OH:44])[CH:34]=[C:35]([S:40](Cl)(=[O:42])=[O:41])[CH:36]=5)[C:30]=4[N:31]=3)[CH:22]=2)[CH:17]=[CH:18][C:19]=1[CH3:20].C(N(CC)CC)C>CN(C=O)C>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[S:40]([C:35]1[CH:36]=[C:37]2[C:32](=[C:33]([OH:44])[CH:34]=1)[C:30]1[N:31]=[C:27]([C:23]3[CH:22]=[C:21]([C:16]4[CH:17]=[CH:18][C:19]([CH3:20])=[C:14]([CH3:13])[CH:15]=4)[CH:26]=[CH:25][CH:24]=3)[NH:28][C:29]=1[CH:39]=[CH:38]2)(=[O:42])=[O:41])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 225666742-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxyl-3H-naphtho[1,2-d]imidazole-7-sulfonyl chloride

Product 1

HCID 69739188(S)-1-[2-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-sulfonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an agitated suspension of (S)-pyrrolidine-2-carboxylic acid tert-butyl ester (0.036 g, 0.21 mmol) in DMF (1 mL) was added 2-(3′,4′-dimethylbiphenyl-3-yl)-9-hydroxyl-3H-naphtho[1,2-d]imidazole-7-sulfonyl chloride (0.064 g, 0.14 mmol) and triethyl amine (0.022 g, 0.21 mmol). After agitated for 15 hrs, the reaction mixture was concentrated under reduced pressure to give (S)-1-[2-(3′,4′-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-sulfonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester. The crude product was treated with 90% trifluoroacetate acid (2 ml). After agitated for 1 hour, the mixture was concentrated under reduced pressure, then subjected to to HPLC (ODS-A, gradient 10-90% CH3CN/water 0.1% TFA) to provide the title compound (0.006 g, 8%) MS(ES) m/z 542 [M+H].

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a7ab20344d9e4e4bb4b1e5769b6239e1
Source dataset
uspto-grants-2005_02
Patent number
US06858630B2

Reaction notes

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