Hydrochloric Acid → HCID 86290885, compound

HRID 525818Notes

Reaction equation

HRID 525818 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[NH:35][C:36]([NH:38][C:39]1[CH:44]=[C:43]([CH3:45])[CH:42]=[CH:41][C:40]=1[F:46])=[O:37])[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[C:13]([C:15]([NH:17][C@@H:18]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:19]([O:21]C)=[O:20])=[O:16])[S:14][C:7]=12.[OH-].[Na+].O.Cl>C1COCC1.CO>[C:28]([O:27][C:25](=[O:26])[CH2:24][CH2:23][C@H:18]([NH:17][C:15]([C:13]1[S:14][C:7]2[C:8](=[N:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]2[CH:32]=[CH:33][C:34]([NH:35][C:36]([NH:38][C:39]3[CH:44]=[C:43]([CH3:45])[CH:42]=[CH:41][C:40]=3[F:46])=[O:37])=[C:2]([F:1])[CH:3]=2)[CH:12]=1)=[O:16])[C:19]([OH:21])=[O:20])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86290886HCID 86290886, compound

Product 1

HCID 86290885HCID 86290885, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of 5-tert-butyl 1-methyl (2S)-2-[({7-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]pentanedioate (260 mg, 0.40 mmol) in a mixture of THF/MeOH (10 ml/10 ml) was added 1M NaOH solution (2 ml, 2 mmol). The mixture was stirred at room temperature for 1 hour and poured into 100 ml of water. 1M HCl was added with stirring until pH=4. The precipitates were filtered, washed with water and dried in vacuo to give (2S)-5-tert-butoxy-2-[({7-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]-5-oxopentanoic acid as off-white solid. Yield: 230 mg, 91%.

Workup

  1. stirringwith stirring until pH=4
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bc27f9aa839c45fa853bcce1e3c7152b
Source dataset
uspto-grants-2016_05
Patent number
US09340555B2

Reaction notes

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