Hydrochloric Acid → HCID 178449829, compound

HRID 2189002Notes

Reaction equation

HRID 2189002 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:17]([CH:18]([OH:36])[CH:19]([O:21][C:22](=[O:35])[CH:23]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:24]([CH3:26])[CH3:25])[CH3:20])[CH2:16][NH:15][C:14]2[NH:13][C:12]([N:37]=CN(C)C)=[N:11][C:10](=[O:42])[C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(=O)(O)[O-].[Na+]>C(#N)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH:17]([CH:18]([OH:36])[CH:19]([O:21][C:22](=[O:35])[CH:23]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:24]([CH3:26])[CH3:25])[CH3:20])[CH2:16][NH:15][C:14]2[NH:13][C:12]([NH2:37])=[N:11][C:10](=[O:42])[C:9]1=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178449828HCID 178449828, compound

Product 1

HCID 178449829HCID 178449829, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The product of step c) (3.1 g, 5.15 mmol) was dissolved in acetonitrile (ACN, 130 ml) and treated with 1N HCl (13 ml, 13 mmol). The mixture was stirred at room temperature until no starting material was present (˜18 h). The reaction mixture was neutralized by addition of a saturated solution of sodium bicarbonate. The solvent was then evaporated in vacuo (temp<40° C.) to give a light yellow solid. The solid was slurried in DCM (50 ml) and filtered. The filtrate was evaporated and the residue purified by flash silica-gel chromatography (gradient elution 0 to 20% methanol in DCM) to give the sub-titled product (1.75 g, 63%, ˜9:1 regioisomeric mixture). 1H NMR (CD3OD) δ 5.10-4.98 (m, 1H), 4.20-4.10 (m, 1H), 4.02-3.90 (m, 1H), 3.72 (d, J=12.3 Hz, 1H), 3.59 (d, J=9.6 Hz, 1H), 3.20 (dd, J=4.5 Hz, J=12.9 Hz, 1H), 2.16-1.96 (m, 1H), 1.46 (s, 9H), 1.42 (s, 9H), 1.30 (d, J=6.6 Hz, 3H), 0.88 (d, J=6.6 Hz, 3H), 0.84 (d, J=6.9 Hz, 3H). MS: ESI (positive): 541 (M+H).

Workup

  1. custom(˜18 h)
  2. customThe solvent was then evaporated in vacuo (temp<40° C.)
  3. customto give a light yellow solid
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue purified by flash silica-gel chromatography (gradient elution 0 to 20% methanol in DCM)

Sources & evidence

ORD record
ord-9dcb5fc1442c4abfb7b0857014df1445
Source dataset
uspto-grants-2012_12
Patent number
US08324210B2

Reaction notes

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