Hydrochloric Acid → HCID 75985946, compound

HRID 417204Notes

Reaction equation

HRID 417204 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([CH:19]2[NH:23][CH:22]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:21]3([C:36]4[C:31](=[CH:32][C:33]([Cl:37])=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:38])[CH:20]2[C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[C:40]=2[F:46])=[O:18])=[CH:12][CH:11]=1)=[O:9])(C)(C)C.Cl>O1CCCC1>[OH:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([CH:19]2[NH:23][CH:22]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:21]3([C:36]4[C:31](=[CH:32][C:33]([Cl:37])=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:38])[CH:20]2[C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[C:40]=2[F:46])=[O:18])=[CH:12][CH:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 76741099rac-(2'S,3'R,4'S,5'R)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid {4-[2-(tert-butyl-dimethyl-silanyloxy)-acetyl]-phenyl}-amide

Product 1

HCID 75985946HCID 75985946, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-(2′S,3′R,4′S,5′R)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid {4-[2-(tert-butyl-dimethyl-silanyloxy)-acetyl]-phenyl}-amide (0.1 g, 0.14 mmol) in tetrahydrofuran (5 mL) was added aqueous HCl solution (1N, 5 mL, 5 mmol). The reaction mixture was stirred at room temperature for 0.5 h. The mixture was concentrated. The residue was partitioned between ethyl acetate and aqueous saturated NaHCO3 solution. The organic layer was separated, washed with water, brine, dried over Na2SO4, then concentrated. The residue was purified by chromatography (silica gel, 5-80% of EtOAc in hexanes) to give rac-(2′S,3′R,4′S,5′R)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid [4-(2-hydroxy-acetyl)-phenyl]-amide as a yellow solid (Yield, 35 mg, 42%).

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and aqueous saturated NaHCO3 solution
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (silica gel, 5-80% of EtOAc in hexanes)
  8. customto give

Sources & evidence

ORD record
ord-512e645c3e1946e3b99f0c11fd1bf43a
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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