Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[4-(3-fluoropropoxy)benzyl]-D-glutamate → (4R)-4-[4-(3-Fluoropropoxy)benzyl]-D-glutamic acid

HRID 591295Notes

Reaction equation

HRID 591295 reaction equation
C(OC([NH:8][C@@H:9]([C:31]([O:33]C(C)(C)C)=[O:32])[CH2:10][C@@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][F:30])=[CH:22][CH:21]=1)[C:12]([O:14]C(C)(C)C)=[O:13])=O)(C)(C)C>FC(F)(F)C(O)=O>[F:30][CH2:29][CH2:28][CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][C@@H:11]([C:12]([OH:14])=[O:13])[CH2:10][C@H:9]([C:31]([OH:33])=[O:32])[NH2:8])=[CH:21][CH:22]=1

Participants

3

Reactant 1

HCID 70674428Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[4-(3-fluoropropoxy)benzyl]-D-glutamate

Product 1

HCID 70673992(4R)-4-[4-(3-Fluoropropoxy)benzyl]-D-glutamic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

60 mg (0.11 mmol) of di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-[4-(3-fluoropropoxy)-benzyl]-D-glutamate were taken up in 3 mL of trifluoro acetic acid and stirred overnight at room temperature. The excess of trifluoro acetic acid was evaporated and the residue was taken up three times in tetrahydrofuran and then evaporated. The resulting oil was chromatographed on C-18 reversed phase silica gel using a water/acetonitrile gradient, the appropriate fractions were combined and concentrated.

Workup

  1. customThe excess of trifluoro acetic acid was evaporated
  2. customevaporated
  3. customThe resulting oil was chromatographed on C-18
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d0103b904c3549ee8b1831d5344eb722
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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