Hydrochloric Acid → HCID 68409375, compound

HRID 2264845Notes

Reaction equation

HRID 2264845 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[NH:19][C@H:18]([C:20]([NH2:22])=[O:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:23]>C(OCC)C>[ClH:23].[C:1]1([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[NH:19][C@H:18]([C:20]([NH2:22])=[O:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59596683HCID 59596683, compound

Product 1

HCID 68409375HCID 68409375, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of (5R)-5-[4-(2-phenylethyl)phenyl]-L-prolinamide (D81, 30 mg, 0.1 mmol) in diethyl ether (2 ml) was added hydrochloric acid (1N in Et2O, 150 μl) and the mixture was triturated. The solvent was removed under vacuum affording the title compound as a white solid (30 mg, 91%). Rt (HPLC): 3.81 min; MS: (ES/+) m/z: 295 [MH]+ C19H22N2O requires 294; 1H NMR (500 MHz, DMSO-d6) δ (ppm): 8.15-8.98 (br.s, 2H); 8.01 (s, 1H); 7.71 (s, 1H); 7.43 (d, 2H); 7.30 (d, 2H); 7.26 (d, 2H); 7.24 (t, 2H); 7.17 (t, 1H); 4.51-4.65 (m, 1H); 4.23-4.33 (m, 1H); 2.81-2.95 (m, 4H); 2.25-2.39 (m, 2H); 2.08-2.20 (m, 1H); 1.92-2.06 (m, 1H).

Workup

  1. customthe mixture was triturated
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-164f8bd305fa44f4b4dc82fe028081ea
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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