di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate → (4S)-4-[4-Hydroxybenzyl]-L-glutamic acid

HRID 591330Notes

Reaction equation

HRID 591330 reaction equation
C(OC([NH:8][C@H:9]([C:27]([O:29]C(C)(C)C)=[O:28])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[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>[OH:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C@H:11]([C:12]([OH:14])=[O:13])[CH2:10][C@@H:9]([C:27]([OH:29])=[O:28])[NH2:8])=[CH:25][CH:24]=1

Participants

3

Reactant 1

HCID 70957078di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate

Product 1

HCID 9899763(4S)-4-[4-Hydroxybenzyl]-L-glutamic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 0.35 g (0.75 mmol) of di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate were added 10 mL of trifluoro acetic acid and the solution was stirred for 2 days 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-cd4a477d37e444a8bfcad166fe4a6042
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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