N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-[(benzyloxycarbonyl)amino]-3-phenylpropyl}-D-alaninamide → N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-amino-3-phenylpropyl}-D-alaninamide

HRID 1849989

Reaction equation

HRID 1849989 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([NH:22][C@@H:23]([C:25]([NH:27][CH2:28][C@H:29]([NH:37]C(OCC1C=CC=CC=1)=O)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:26])[CH3:24])=[O:21])[CH2:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=1[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([NH:22][C@@H:23]([C:25]([NH:27][CH2:28][C@H:29]([NH2:37])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:26])[CH3:24])=[O:21])[CH2:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=1[CH3:19])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 71212286N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-[(benzyloxycarbonyl)amino]-3-phenylpropyl}-D-alaninamide

Product 1

HCID 71229909N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-amino-3-phenylpropyl}-D-alaninamideYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-[(benzyloxycarbonyl)amino]-3-phenylpropyl}-D-alaninamide (314 mg, 0.46 mmol) was dissolved in 5 mL of tetrahydrofuran and degassed by bubbling through argon gas for a few minutes. Palladium on charcoal (10% w/w, 5 mg) was added and the suspension stirred for 16 h at room temperature under 1 atmosphere of hydrogen pressure. The mixture was filtered through a short pad of celite, washed with 5 mL of tetrahydrofuran and evaporated under reduced pressure. The resulting residue was purified by column chromatography using 5% methanol in dichloromethane as eluant to provide the title compound as a clear oil (203 mg, 82%).

Workup

  1. customdegassed
  2. customby bubbling through argon gas for a few minutes
  3. additionPalladium on charcoal (10% w/w, 5 mg) was added
  4. filtrationThe mixture was filtered through a short pad of celite
  5. washwashed with 5 mL of tetrahydrofuran
  6. customevaporated under reduced pressure
  7. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-e3af8f8542bf4285bd21760093709987
Source dataset
uspto-grants-2015_02
Patent number
US08957025B2

Linked notes

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