Trifluoroacetic acid → HCID 178426693, compound

HRID 1823935Notes

Reaction equation

HRID 1823935 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:32][C:33]1[C:38]([CH3:39])=[CH:37][C:36]([C:40](=[O:42])[NH2:41])=[CH:35][C:34]=1[CH3:43])[C:9](=[O:31])[N:10]1[CH:19]([C:20]2[NH:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][CH:8]([C:9](=[O:31])[N:10]1[CH:19]([C:20]2[NH:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)[CH2:32][C:33]1[C:34]([CH3:43])=[CH:35][C:36]([C:40]([NH2:41])=[O:42])=[CH:37][C:38]=1[CH3:39]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178426696HCID 178426696, compound

Product 1

HCID 178426693HCID 178426693, compoundYield 28%

Procedure

To 0.8 mmol of {1-(4-carbamoyl-2,6-dimethyl-benzyl)-2-oxo-2-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid tert-butyl ester cooled in an ice bath under argon, was added 3 mL of trifluoroacetic acid. After stirring for 3 hours, the reaction mixture was concentrated and purified on a Gilson prep LC system. Obtained 79 mg (0.13 mmol) of the pure S,S isomer of 4-{2-amino-3-oxo-3-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-propyl}-3,5-dimethyl-benzamide and 58 mg (0.09 mmol) of a mix of diastereomers for a total of 137 mg (0.22 mmol, 28% yield). Data for “pure” isomer (may contain a trace of other isomer as evident by tlc): 1H NMR (300 MHz, CD3OD): δ 1.85 (0.5H, dd), 2.13–2.51 (6H, m), 2.91 (0.4H, dd), 3.18–3.52 (4H, m), 3.70 (0.5H, d), 4.28–4.47 (1H, m), 4.60–5.06 (2.5H, m), 5.62 (0.5H, t), 6.95–7.90 (13H, m).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified on a Gilson prep LC system

Sources & evidence

ORD record
ord-6ed7afd9d71d455ab82981c8c5777152
Source dataset
uspto-grants-2006_05
Patent number
US07041681B2

Reaction notes

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