Trifluoroacetic acid → HCID 72406547, compound

HRID 720195Notes

Reaction equation

HRID 720195 reaction equation
C(OC([N:8]1[CH:17]([C:18](=[O:47])[NH:19][CH:20]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)[C:21]([N:23]2[CH2:27][CH:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:25][CH:24]2[CH2:36][CH:37]=[CH2:38])=[O:22])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:36]([CH:24]1[CH2:25][CH:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:27][N:23]1[C:21](=[O:22])[CH:20]([NH:19][C:18]([CH:17]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][NH:8]1)=[O:47])[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=1)[CH:37]=[CH2:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69587330HCID 69587330, compound

Product 1

HCID 72406547HCID 72406547, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[2-(2-Allyl-4-benzyloxy-pyrrolidin-1-yl)-1-(4-fluorobenzyl)-2-oxo-ethylcarbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester, 55, (200 mg) is dissolved into CH2Cl2 (3 mL) and trifluoroacetic acid (1 mL) is added. The reaction mixture is stirred for 5 hours and concentrated. The residue is purified by reverse phase HPLC to afford 50 mg of the desired product. 1H NMR (CDCl3, 300 MHz) δ 6.80˜7.50 (m, 13H), 5.75 (m, 1H), 5.06 (m, 2H), 4.30˜4.70 (m, 6H), 4.06 (m, 2H), 3.75 (m, 1H), 2.90˜3.30 (m, 6H), 2.69 (m, 1H), 2.23 (m, 1H), 1.80˜2.00 (m, 2H); MS (ES-MS) m/z 542 (M+1).

Workup

  1. additionis added
  2. concentrationconcentrated
  3. customThe residue is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-28acfb1884604d54bb5f551d88cbac66
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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