Hydrogen chloride-ethyl acetate → HCID 67442257, compound

HRID 1400889Notes

Reaction equation

HRID 1400889 reaction equation
[CH:1]1([NH:4][C:5](=[O:37])[NH:6][C:7]2[CH:35]=[CH:34][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[CH2:26][CH2:25][N:24](C(OCCCC)=O)[CH2:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:36])[CH:8]=2)[CH2:3][CH2:2]1.[ClH:38].CCOC(C)=O>CCOC(C)=O>[ClH:38].[ClH:38].[CH:1]1([NH:4][C:5]([NH:6][C:7]2[CH:35]=[CH:34][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[CH2:26][CH2:25][NH:24][CH2:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:36])[CH:8]=2)=[O:37])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86658596HCID 86658596, compound

Product 1

HCID 67442257HCID 67442257, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 270 (996 mg, 1.90 mmol) in EtOAc (20 mL) was added 1N HCl-EtOAc (11.4 mL, 11.4 mmol). The reaction mixture was stirred for 18 hours, the precipitate was collected by filtration, washed with EtOAc (30 mL) and dried to afford title compound 271 (962 mg, 100% yield) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 9.22 (br, 2H), 9.03 (s, 1H), 8.58 (d, J=6.0 Hz, 1H), 7.74 (dd, J=13.5, 2.7 Hz, 1H), 7.70 (s, 1H), 7.38 (t, =9.0 Hz, 1H), 7.25-7.15 (m, 1H), 6.77 (d, J=6.0 Hz, 1H), 6.72 (s, 1H), 6.47 (s, 1H), 4.80-4.30 (br, 1H), 3.85-3.75 (m, 2H), 3.42-3.31 (m, 2H), 2.90-2.80 (m, 2H), 2.60-2.40 (m, 1H), 0.70-0.60 (m, 2H), 0.48-0.35 (m, 2H).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with EtOAc (30 mL)
  3. customdried

Sources & evidence

ORD record
ord-60303758d8004ccf9414a00d7fe4a695
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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