Hydrochloric Acid → HCID 86705479, compound

HRID 2279461Notes

Reaction equation

HRID 2279461 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:10](=[O:20])[CH2:9]2)=[CH:4][C:3]=1[F:21].[Li+].[OH-:23].Cl>C1COCC1.O>[C:16]([O:15][C:13]([NH:11][CH2:12][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:21])[CH:4]=1)[CH2:9][C:10]([OH:23])=[O:20])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86705478HCID 86705478, compound

Product 1

HCID 86705479HCID 86705479, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 92 (912 mg, 2.91 mmol) in THF/H2O (2:1; 15 mL) was added solid LiOH (209 mg, 8.72 mmol). The reaction mixture was stirred at RT for 18 h. The reaction mixture was acidified with 1M HCl to ca. pH 2-3 then twice extracted with EtOAc. The combined EtOAc layers were dried (Na2SO4), filtered and concentrated to afford 902 mg (93.5%) of (S)-4-(tert-butoxycarbonylamino)-3-(4-chloro-3-fluorophenyl)butanoic acid (100) which was used without further purification.

Workup

  1. extractionthen twice extracted with EtOAc
  2. dry with materialThe combined EtOAc layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-82953bca051b413fb67871a7b88fb1a2
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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