Triethylamine → methyl 2-{4-[(N-[(allyloxy)carbonyl]-4-{{2-[(benzhydryloxy)carbonyl]phenyl}[tert-butoxy(oxo)acetyl]amino}-L-phenylalanyl)amino]butoxy}-6-hydroxybenzoate

HRID 488660Notes

Reaction equation

HRID 488660 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@H:8]([C:48]([OH:50])=O)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([O:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[C:17](=[O:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:12][CH:11]=1)=[O:6])[CH:2]=[CH2:3].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[NH2:83][CH2:84][CH2:85][CH2:86][CH2:87][O:88][C:89]1[CH:98]=[CH:97][CH:96]=[C:95]([OH:99])[C:90]=1[C:91]([O:93][CH3:94])=[O:92].C(N(CC)CC)C>CN(C=O)C.O>[CH2:1]([O:4][C:5]([NH:7][C@H:8]([C:48]([NH:83][CH2:84][CH2:85][CH2:86][CH2:87][O:88][C:89]1[CH:98]=[CH:97][CH:96]=[C:95]([OH:99])[C:90]=1[C:91]([O:93][CH3:94])=[O:92])=[O:50])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([O:34][CH:35]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33])[C:17](=[O:25])[C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])=[CH:14][CH:15]=1)=[O:6])[CH:2]=[CH2:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 10919495N-[(allyloxy)carbonyl]-4-{{2-[(benzhydryloxy)carbonyl]phenyl}[tert-butoxy(oxo)acetyl]amino}-L-phenylalanineHCID 11832643Methyl 2-(4-aminobutoxy)-6-hydroxybenzoate

Product 1

HCID 11029331methyl 2-{4-[(N-[(allyloxy)carbonyl]-4-{{2-[(benzhydryloxy)carbonyl]phenyl}[tert-butoxy(oxo)acetyl]amino}-L-phenylalanyl)amino]butoxy}-6-hydroxybenzoateYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of N-[(allyloxy)carbonyl]-4-{{2-[(benzhydryloxy)carbonyl]phenyl}[tert-butoxy(oxo)acetyl]amino}-L-phenylalanine (100 mg, 0.147 mmol), TBTU (67 mg, 0.206 mmol), and HOBT (3 mg, 0.02 mmol) in DMF (2 mL) was added methyl 2-(4-aminobutoxy)-6-hydroxybenzoate, followed by addition of triethylamine (75 μL, 0.53 mmol). The resulting mixture was then stirred at ambient temperature for 2 hours, diluted with the addition of water. The crude product was extracted with ethyl acetate (2×10 mL). The combined organic layer were washed with aqueous NaHCO3 (2×25 mL) and brine (2×25 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting residue was purified on an AllTech sep-pak to provide the titled compound (89 mg, 68%).

Workup

  1. extractionThe crude product was extracted with ethyl acetate (2×10 mL)
  2. washThe combined organic layer were washed with aqueous NaHCO3 (2×25 mL) and brine (2×25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified on an AllTech sep-pak

Sources & evidence

ORD record
ord-6b981449fe5547f199bd2e41f692014e
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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