Sodium Bicarbonate → HCID 68590716, compound

HRID 736930Notes

Reaction equation

HRID 736930 reaction equation
[C:1]([O-:4])(O)=[O:2].[Na+].[NH2:6][C@H:7]([CH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[C:15]([NH2:22])=[C:14]([Cl:23])[CH:13]=1)[C:8]([OH:10])=[O:9]>O.C1COCC1>[NH2:22][C:15]1[C:16]([C:18]([F:20])([F:21])[F:19])=[CH:17][C:12]([CH2:11][C@@H:7]([NH:6][C:1]([O:4][C:12]([CH3:17])([CH3:13])[CH3:11])=[O:2])[C:8]([OH:10])=[O:9])=[CH:13][C:14]=1[Cl:23]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 68590975HCID 68590975, compound

Product 1

HCID 68590716HCID 68590716, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.71 g (35.0 mmol) of NaHCO3 in 100 mL water was added to a solution of 6.5 g (23.0 mmol) of (R)-2-amino-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-propionic acid in 140 mL of THF. 15.28 g (70.0 mmol) of Boc-anhydride was added and the mixture was stirred for 3 h at RT. THF was evaporated off i. vac., the aqueous phase was washed with EtOAc and acidified with 10% citric acid solution. The aqueous phase was exhaustively extracted with EtOAc, the combined org. extracts were dried over Na2SO4 and evaporated down i. vac. The crude product was used in the next reaction step without any further purification.

Workup

  1. customTHF was evaporated off i
  2. wash, the aqueous phase was washed with EtOAc
  3. extractionThe aqueous phase was exhaustively extracted with EtOAc
  4. dry with materialextracts were dried over Na2SO4
  5. customevaporated down i
  6. customThe crude product was used in the next reaction step without any further purification

Sources & evidence

ORD record
ord-8c61f7f4bbb1429599a0122c6da2d604
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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