Hydrochloric Acid → HCID 178472056, compound

HRID 391249Notes

Reaction equation

HRID 391249 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([C:10](=[O:29])[C:11]1[CH:16]=[C:15]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[F:25])[C:14]([O:26][CH3:27])=[CH:13][C:12]=1[F:28])=[CH:6]N(C)C)[CH3:2].[NH2:31][C@@H:32]([CH:35]([CH3:37])[CH3:36])[CH2:33][OH:34].Cl>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:30])[C:5]([C:10](=[O:29])[C:11]1[CH:16]=[C:15]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[F:25])[C:14]([O:26][CH3:27])=[CH:13][C:12]=1[F:28])=[CH:6][NH:31][C@H:32]([CH2:33][OH:34])[CH:35]([CH3:37])[CH3:36])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 640993L-ValinolHCID 689553422-(5-(3-Chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl)-3-dimethylaminoacrylic acid ethyl ester

Product 1

HCID 178472056HCID 178472056, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(5-(3-chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl)-3-dimethylaminoacrylic acid ethyl ester prepared in Step XII in toluene was added (S)-2-amino-3-methylbutan-1-ol (3.96 g) with stirring at room temperature. After stirring for 30 min, 1N hydrochloric acid (60 ml) was added, and the mixture was further stirred for 1 hr. The organic layer was separated, and washed successively with water (60 ml), 5% sodium hydrogencarbonate (60 ml) and water (60 ml). The organic layer was concentrated under reduced pressure. N,N-dimethylformamide (40 ml) was added to the residue, and the mixture was concentrated again under reduced pressure. The residue was dissolved in N,N-dimethylformamide (60 ml) to give a solution of 2-(5-(3-chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl)-3-((S)-1-hydroxymethyl-2-methylpropylamino)acrylic acid ethyl ester in N,N-dimethylformamide. This was identified as the title compound by HPLC.

Workup

  1. stirringAfter stirring for 30 min
  2. stirringthe mixture was further stirred for 1 hr
  3. customThe organic layer was separated
  4. washwashed successively with water (60 ml), 5% sodium hydrogencarbonate (60 ml) and water (60 ml)
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. additionN,N-dimethylformamide (40 ml) was added to the residue
  7. concentrationthe mixture was concentrated again under reduced pressure
  8. dissolutionThe residue was dissolved in N,N-dimethylformamide (60 ml)

Sources & evidence

ORD record
ord-6049271186444828b205a46df473cfc5
Source dataset
uspto-grants-2013_02
Patent number
US08383819B2

Reaction notes

Loading…