Anisole → (4S)-4-[4-(3-Fluoropropoxy)benzyl]-L-glutamic acid

HRID 591257Notes

Reaction equation

HRID 591257 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.COC1C=CC=CC=1>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

4

Reactant 2

HCID 7519AnisoleHCID 70674426Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-[4-(3-fluoropropoxy)benzyl]-L-glutamate

Product 1

HCID 70673991(4S)-4-[4-(3-Fluoropropoxy)benzyl]-L-glutamic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

60 mg (0.11 mmol) of di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-[4-(3-fluoropropoxy)-benzyl]-L-glutamate were taken up in 2 mL of trifluoro acetic acid and 1 mL of methoxybenzene 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-0349f2d6fae5428db3c0bde678ea5c77
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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