Ammonium Chloride → HCID 68029042, compound

HRID 714141Notes

Reaction equation

HRID 714141 reaction equation
[OH:1][CH2:2][C@@H:3]([N:35]([CH2:48][CH2:49][CH:50]([CH3:52])[CH3:51])[S:36]([C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-])=O)=[CH:41][CH:40]=1)(=[O:38])=[O:37])[CH2:4][S:5][C:6]1[CH:11]=[CH:10][NH:9][C:8](=[O:12])[C:7]=1[NH:13][C:14](=[O:34])[C@H:15]([CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:16][C:17]([O:19][CH3:20])=[O:18].[Cl-].[NH4+]>C(O)C.C1COCC1.O.[Fe]>[NH2:45][C:42]1[CH:41]=[CH:40][C:39]([S:36]([N:35]([CH2:48][CH2:49][CH:50]([CH3:52])[CH3:51])[C@H:3]([CH2:2][OH:1])[CH2:4][S:5][C:6]2[CH:11]=[CH:10][NH:9][C:8](=[O:12])[C:7]=2[NH:13][C:14](=[O:34])[C@H:15]([CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:16][C:17]([O:19][CH3:20])=[O:18])(=[O:38])=[O:37])=[CH:44][CH:43]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 86708036HCID 86708036, compound

Product 1

HCID 68029042HCID 68029042, compoundYield 45.6%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
74 °C

Procedure

A solution of N-(4-{[(2R)-3-hydroxy-2-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}propyl]sulfanyl}-2-oxo-1,2-dihydropyridin-3-yl)-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (50, 61.3 mg, 0.082 mmol) in ethanol (3 ml), THF (1.5 ml) and water (0.8 mL) was treated with saturated solution of ammonium chloride (298 mg, 5.57 mmol) in water (0.8 mL) followed by addition of powdered iron (80 mg, 1.433 mmol). The mixture was degassed and stirred under N2 at external temperature of 74° C. for 90 min. Diluted with DCM, washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated. Purification performed in a column of silicagel eluted with 5% to 35% MeOH in DCM to afford the title compound (27 mg, 45% yield) as pale yellow foam. MS: m/z=722.2 (MH+).

Workup

  1. customThe mixture was degassed
  2. additionDiluted with DCM
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. washof silicagel eluted with 5% to 35% MeOH in DCM

Sources & evidence

ORD record
ord-cb3fe1d00b9e45d589ac7fc695e8509b
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

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