Hydrochloric Acid → HCID 66624999, compound

HRID 417376Notes

Reaction equation

HRID 417376 reaction equation
C([O:3][C:4](=[O:44])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C@@H:16]2[NH:20][C@@H:19]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C@:18]3([C:33]4[C:28](=[CH:29][C:30]([Cl:34])=[CH:31][CH:32]=4)[NH:27][C:26]3=[O:35])[C@H:17]2[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[C:37]=2[F:43])=[O:15])=[CH:9][CH:8]=1)C.Cl>C1COCC1.O.C(OCC)(=O)C>[Cl:34][C:30]1[CH:29]=[C:28]2[NH:27][C:26](=[O:35])[C@:18]3([C@@H:17]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[C:37]=4[F:43])[C@H:16]([C:14]([NH:13][C:10]4[CH:11]=[CH:12][C:7]([NH:6][CH2:5][C:4]([OH:44])=[O:3])=[CH:8][CH:9]=4)=[O:15])[NH:20][C@H:19]3[CH2:21][C:22]([CH3:24])([CH3:23])[CH3:25])[C:33]2=[CH:32][CH:31]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66625488HCID 66625488, compound

Product 1

HCID 66624999HCID 66624999, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of rac-(4-{[(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′-carbonyl]-amino}-phenylamino)-acetic acid ethyl ester (28 mg, 0.043 mmol) in THF (3 mL) was added LiOH monohydrate (9 mg, 0.199 mmol) in water (1.5 mL) and the reaction mixture was allowed to stir at rt overnight. The mixture was then treated with 1N HCl to slightly acidic, diluted with ethyl acetate (80 mL), washed with water (2×15 mL), dried with Na2SO4 and concentrated to give rac-(4-{[(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′-carbonyl]-amino}-phenylamino)-acetic acid as a white solid (25 mg, 97%). MS (ES+) m/z [(M+H)+]: 613

Workup

  1. washwashed with water (2×15 mL)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-48fddf38864f470d895ab2c8fb890c58
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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