Methanesulfonic Acid → HCID 67458340, compound

HRID 554819Notes

Reaction equation

HRID 554819 reaction equation
C(O[C:6]([NH:8][CH2:9][C@H:10]([CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])[C:11]([OH:13])=[O:12])=O)(C)(C)C.CS(O)(=O)=O.[CH3:29][O:30][C:31]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[C:35]([O:41][CH3:42])[C:32]=1C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(OCC)(=O)C.C(N(CC)CC)C>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]([O:22][CH3:23])=[C:15]([CH:20]=1)[CH2:14][C@@H:10]([CH2:9][NH:8][CH2:6][C:32]1[C:35]([O:41][CH3:42])=[CH:36][C:37]([O:39][CH3:40])=[CH:38][C:31]=1[O:30][CH3:29])[C:11]([OH:13])=[O:12]

Participants

8

Reactant 5

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 700192,4,6-TrimethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66935162(2S)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoic acid

Product 1

HCID 67458340HCID 67458340, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propionic acid (10g) was dissolved in ethyl acetate (120 ml), then methane sulfonic acid (9.4 ml) was added at room temperature, and the resulting mixture was stirred at that temperature for 2 hours. To the reaction solution was added triethylamine (20.3 ml), and the mixture was stirred for 13 hours. Then 2,4,6-trimethoxybenzaldehyde (5.7 g) was added and the mixture was stirred for 30 minutes. Next, to the reaction solution, sodium triacetoxyborohydride (9.3 g) was added and the mixture was stirred for 2 hours. To the reaction solution, a 1N aqueous sodium hydroxide solution was added, and the layers were separated. The aqueous layer was extracted again with ethyl acetate. The organic layer was washed with a 1N aqueous sodium hydroxide solution, then the appeared precipitated crystals were collected by filtration and dried to obtain the title compound (11.5 g) as a colorless crystal.

Workup

  1. stirringthe mixture was stirred for 13 hours
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringthe mixture was stirred for 2 hours
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted again with ethyl acetate
  6. washThe organic layer was washed with a 1N aqueous sodium hydroxide solution
  7. customthe appeared precipitated crystals
  8. filtrationwere collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-a936a41559074d77bac253747f5ebdbc
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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