Trifluoroacetic acid → HCID 86620596, compound

HRID 504162Notes

Reaction equation

HRID 504162 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC(=O)[NH:14][C@H:15]([C:31]1[NH:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[N:32]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)(C)(C)C>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[NH:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=[C:31]1[C@@H:15]([NH3+:14])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66751078HCID 66751078, compound

Product 1

HCID 86620596HCID 86620596, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.063 mL, 0.82 mmol) was added to a room temperature solution of [(S)-1-(1H-Benzimidazol-2-yl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (0.073 g, 0.16 mmol) in CH2Cl2 (10 mL). The resulting solution was stirred at room temperature for 2 hours, and then concentrated in vacuo to give (S)-1-(1H-Benzimidazol-2-yl)-2-(4-benzyloxy-phenyl)-ethylammonium trifluoro-acetate as a red-brown oil. This material was re-suspended in CH2Cl2 (4 mL) and treated with a room temperature solution of PyBOP (0.086 g, 0.16 mmoles), triethylamine (0.080 mL, 0.58 mmol), and (S)-1-(3-Trifluoromethyl-benzenesulfonyl)-piperidine-2-carboxylic acid (0.056 g, 0.16 mmol) in CH2Cl2 (4 mL). The resulting mixture was stirred at room temperature for 16 h. Purification of the product by flash chromatography on silica gel eluting with 10-50% EtOAc/heptane afforded 0.075 g (69%) of the title compound as a colorless powder: ES+ LC/MS m/e 663 (M+H), 100% purity; 1H NMR (CDCl3) ˜1:1 mixture of diastereomers δ10.07 (bd s, 1), 8.07 (s, 1), 7.95 (d, 1, J=7.8 Hz), 7.81 (m, 1), 7.60 (m, 1), 7.24-7.42 (m, 9), 7.10 (d, 2, J=8.6 Hz), 6.88 (d, 2, J=8.6 Hz), 5.25-5.42 (m, 1), 5.04 (s, 2), 4.48 (bd s, 1), 3.32-3.84 (m, 3), 2.88 (m, 1), 1.05-1.77 (m, 6).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fb39daa46bf484eb10acea680676f4a
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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