Chloride → HCID 178473384, compound

HRID 576546Notes

Reaction equation

HRID 576546 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:39])[C@@H:13]([NH2:38])[CH2:14][CH2:15][CH2:16][NH:17]/[C:18](/[NH2:37])=[N:19]/[S:20]([C:23]2[C:24]([CH3:36])=[C:25]([CH3:35])[C:26]3[O:30][C:29]([CH3:32])([CH3:31])[CH2:28][C:27]=3[C:33]=2[CH3:34])(=[O:22])=[O:21])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[OH-].[Na+].[Cl-].[OH:43][S:44]([OH:47])(=O)=O.[CH2:48]1[CH2:52]O[CH2:50][CH2:49]1>O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:39])[C@@H:13]([NH:38][S:44]([C:48]2[C:52]([CH:25]([CH3:26])[CH3:35])=[CH:24][C:23]([CH:33]([CH3:27])[CH3:34])=[CH:50][C:49]=2[CH:13]([CH3:14])[CH3:12])(=[O:47])=[O:43])[CH2:14][CH2:15][CH2:16][NH:17]/[C:18](/[NH2:37])=[N:19]/[S:20]([C:23]2[C:24]([CH3:36])=[C:25]([CH3:35])[C:26]3[O:30][C:29]([CH3:31])([CH3:32])[CH2:28][C:27]=3[C:33]=2[CH3:34])(=[O:22])=[O:21])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 312ChlorideHCID 1118Sulfuric AcidHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 178473398HCID 178473398, compound

Product 1

HCID 178473384HCID 178473384, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of compound G (1.0 g, 1.8 mmol) in THF (7 mL) was added 3.1N aqueous NaOH (4.0 mL) and stirred for 5 min. The reaction mixture was cooled to ˜5° C., and then a solution of tripsyl chloride added drop wise (2.2 g, 7.3 mmol) in THF (5 mL) and stirred at room temperature overnight (˜18 h). The reaction mixture was diluted with H2O (130 mL), acidified with 2% H2SO4 (15 mL) and extracted with EtOAc (3×80 mL). Organic layer were combined and washed with H2O (2×400 mL), saturated NaHCO3 (100 mL), H2O (200 mL) and brine (200 mL). The organic layer was separated dried over MgSO4 and solvent removed in vacuo to afford (2.9 g) of crude product. This was purified by normal phase flash chromatography (5-10% MeOH/DCM) to afford compound H (0.52 g, 1.0 mmol). LC-MS [M+H] 833.8 (C41H64N6O8S2+H, calc: 834.1).

Workup

  1. extractionextracted with EtOAc (3×80 mL)
  2. washwashed with H2O (2×400 mL), saturated NaHCO3 (100 mL), H2O (200 mL) and brine (200 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4 and solvent
  5. customremoved in vacuo
  6. customto afford (2.9 g) of crude product
  7. customThis was purified by normal phase flash chromatography (5-10% MeOH/DCM)

Sources & evidence

ORD record
ord-e5bddd1594fc4577985a9258c570dfa0
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

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