Hydrochloric Acid → HCID 178493272, compound

HRID 630387Notes

Reaction equation

HRID 630387 reaction equation
[OH:1][C:2]([C:42]1[S:43][CH:44]=[CH:45][CH:46]=1)([C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([CH2:27][O:28][Si](C(C)(C)C)(C)C)=[CH:21][C:20]=2[Cl:36])=[O:17])[CH3:13])[CH2:8][CH2:7]1)=[O:4].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:1][C:2]([C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)([C:42]1[S:43][CH:44]=[CH:45][CH:46]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([CH2:27][OH:28])=[CH:21][C:20]=2[Cl:36])=[O:17])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178493273HCID 178493273, compound2×

Product 1

HCID 178493272HCID 178493272, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-4-((3-(4-((tert-butyl(dimethyl)silyloxy)methyl)-2-chloro-5-methoxyphenylamino)-3-oxopropyl)(methyl)amino)cyclohexyl hydroxy(di-2-thienyl)-acetate (intermediate 41; 0.76 mg, 1.08 mmol) in tetrahydrofuran (19 mL) was added hydrochloric acid 1M (3.25 mL, 3.25 mmol). The mixture was stirred at room temperature for 3 hours. The reaction mixture was neutralized by a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The crude obtained was purified by column chromatography with silica gel, eluting with chloroform/methanol 50/1 to give the title compound as an oil (84%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe crude obtained
  3. customwas purified by column chromatography with silica gel
  4. washeluting with chloroform/methanol 50/1

Sources & evidence

ORD record
ord-99c4332fbbed4a94b8429ecedc0617cf
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

Loading…