Hydrogen chloride-ethyl acetate → HCID 67442370, compound

HRID 1400964Notes

Reaction equation

HRID 1400964 reaction equation
[CH:1]1([NH:4][C:5](=[O:48])[NH:6][C:7]2[CH:46]=[CH:45][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:26]=[CH:25][C:24]([CH2:27][N:28]([CH:32]6[CH2:37][CH2:36][N:35](C(OCCCC)=O)[CH2:34][CH2:33]6)[C:29](=[O:31])[CH3:30])=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:47])[CH:8]=2)[CH2:3][CH2:2]1.Cl.CCOC(C)=O>CCOC(C)=O>[CH:1]1([NH:4][C:5](=[O:48])[NH:6][C:7]2[CH:46]=[CH:45][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:26]=[CH:25][C:24]([CH2:27][N:28]([CH:32]6[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]6)[C:29](=[O:31])[CH3:30])=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:47])[CH:8]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86658605HCID 86658605, compound

Product 1

HCID 67442370HCID 67442370, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 608 (0.314 g, 0.465 mmol) in EtOAc (6 mL) was added 1N HCl-EtOAc (2.0 ml, 2.0 mmol) at RT. The reaction mixture was stirred overnight then concentrated and co-evaporated with EtOAc. The residue was purified by flash chromatography using Hi-Flash column (Yamazen Corporation) packed with amino silica gel (DCM/MeOH:96/4 to 80/20) to afford title compound 609 (0.193 g, 72% yield) as a white amorphous solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 8.71 (s, 1H), 8.54-8.46 (m, 2H), 8.34 (s, 0.3H), 8.30 (s, 0.7H), 8.26 (d, J=8.1 Hz, 0.3H), 8.18 (d, J=8.1 Hz, 0.7H), 7.82-7.69 (m, 2H), 7.38 (t, J=9.0 Hz, 1H), 7.25-7.15 (m, 1H), 6.68-6.62 (m, 1H), 6.57 (d, J=3.0 Hz, 1H), 4.66 (s, 0.7H), 4.54 (s, 1.3H), 3.90-3.75 (m, 1H), 3.00-2.90 (m, 2H), 2.61-2.40 (m, 3H), 2.20 (s, 2H), 1.99 (s, 1H), 1.65-1.40 (m, 4H), 0.71-0.62 (m, 2H), 0.48-0.40 (m, 2H).

Workup

  1. concentrationthen concentrated
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e051c66771664ca3951add3e4ab5008d
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

Loading…