Hydrochloric Acid → N-((1S,2R)-1-(3,5-difluorobenzyl)-3-{[6-ethyl-3,4-dihydro-2H-chromen-4-yl]amino}-2-hydroxypropyl)acetamide

HRID 1991494Notes

Reaction equation

HRID 1991494 reaction equation
CC(OC)(C)C.C(Cl)Cl.[F:10][C:11]1[CH:12]=[C:13]([CH:36]=[C:37]([F:39])[CH:38]=1)[CH2:14][C@H:15]([NH:32][C:33](=[O:35])[CH3:34])[C@H:16]([OH:31])[CH2:17][NH:18][C@@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH2:29][CH3:30])[CH:27]=2)[O:22][CH2:21][CH2:20]1.Cl>CCOCC.CO>[F:10][C:11]1[CH:12]=[C:13]([CH:36]=[C:37]([F:39])[CH:38]=1)[CH2:14][C@H:15]([NH:32][C:33](=[O:35])[CH3:34])[C@H:16]([OH:31])[CH2:17][NH:18][CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH2:29][CH3:30])[CH:27]=2)[O:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 15413tert-Butyl methyl etherHCID 10319857N-((1S,2R)-1-(3,5-difluorobenzyl)-3-{[(4S)-6-ethyl-3,4-dihydro-2H-chromen-4-yl]amino}-2-hydroxypropyl)acetamide

Product 1

HCID 60206817N-((1S,2R)-1-(3,5-difluorobenzyl)-3-{[6-ethyl-3,4-dihydro-2H-chromen-4-yl]amino}-2-hydroxypropyl)acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a MTBE (20 ml), CH2Cl2 (5 ml), MeOH (0.5 ml) solution of N-((1S,2R)-1-(3,5-difluorobenzyl)-3-{[(4S)-6-ethyl-3,4-dihydro-2H-chromen-4-yl]amino}-2-hydroxypropyl)acetamide (0.2 g, 0.5 mmol) was added 1N HCl in Et2O (0.38 ml) and the mixture stirred at room temperature. The final white solid was isolated by removing the solvent and tritration with Et2O. HRMS (ESI+) calcd for C23H28F2N2O3 m/z 419.2146 (M+H)+. Found 419.2166.

Workup

  1. customThe final white solid was isolated
  2. customby removing the solvent and tritration with Et2O

Sources & evidence

ORD record
ord-20a15cef86314725b44bd248cb97fe57
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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