Resorcinol → 2-[{4-[(2S)-2-{[(Allyloxy)carbonyl]amino}-3-({4-[3-hydroxy-2-(methoxycarbonyl)phenoxy]butyl}amino)-3-oxopropyl]phenyl}(carboxycarbonyl)amino]benzoic acid

HRID 488661Notes

Reaction equation

HRID 488661 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@H:8]([C:48]([NH:50][CH2:51][CH2:52][CH2:53][CH2:54][O:55][C:56]1[CH:65]=[CH:64][CH:63]=[C:62]([OH:66])[C:57]=1[C:58]([O:60][CH3:61])=[O:59])=[O:49])[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]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:33])[C:17](=[O:25])[C:18]([O:20]C(C)(C)C)=[O:19])=[CH:12][CH:11]=1)=[O:6])[CH:2]=[CH2:3].C1(C=CC=C(O)C=1)O.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:4][C:5]([NH:7][C@H:8]([C:48]([NH:50][CH2:51][CH2:52][CH2:53][CH2:54][O:55][C:56]1[CH:65]=[CH:64][CH:63]=[C:62]([OH:66])[C:57]=1[C:58]([O:60][CH3:61])=[O:59])=[O:49])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]([C:17]([C:18]([OH:20])=[O:19])=[O:25])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([OH:34])=[O:33])=[CH:14][CH:15]=1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 6422Trifluoroacetic acidHCID 11029331methyl 2-{4-[(N-[(allyloxy)carbonyl]-4-{{2-[(benzhydryloxy)carbonyl]phenyl}[tert-butoxy(oxo)acetyl]amino}-L-phenylalanyl)amino]butoxy}-6-hydroxybenzoate

Product 1

HCID 103053012-[{4-[(2S)-2-{[(Allyloxy)carbonyl]amino}-3-({4-[3-hydroxy-2-(methoxycarbonyl)phenoxy]butyl}amino)-3-oxopropyl]phenyl}(carboxycarbonyl)amino]benzoic acidYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture methyl 2-{4-[(N-[(allyloxy)carbonyl]-4-{{2-[(benzhydryloxy)carbonyl]phenyl}[tert-butoxy(oxo)acetyl]amino}-L-phenylalanyl)amino]butoxy}-6-hydroxybenzoate (89 mg, 0.10 mmol), 20 mg of resorcinol, and trifluoroacetic acid (1.5 mL) in methylene chloride (2.0 mL) was stirred for 5 hours, concentrated under reduced pressure. The crude product was purified on a Gilson preparative HPLC to provide the titled compound as a white powder (35 mg, 0.052 mmol, 52%). MS (ESI+) m/e 678 (M+H)+, 1H NMR (300 MHz, DMSO-d6) 1.40-1.66 (m, 4H), 2.68-2.83 (m, 1H), 2.83-2.98 (m, 1H), 2.98-3.15 (m, 2H), 3.72 (s, 3H), 3.90 (t, J=5.85 Hz, 1H), 4.09-4.12 (m, 1H), 4.33-4.41 (m, 2H), 5.08 (d, J=10.8 Hz, 1H), 5.18 (d, J=18.0 Hz, 1H), 5.70-5.90 (m, 1H), 6.47 (d, J=8.7 Hz, 1H), 7.25 (d, J=8.7 Hz, 1H), 7.29 (d, J=8.7 Hz, 1H), 7.36 (d, J=8.7 Hz, 1H), 7.38-7.66 (m, 3H), 7.93-8.03 (m, 2H), 9.92 (s, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified on a Gilson preparative HPLC

Sources & evidence

ORD record
ord-f8993e9cf3fa444dae0ac4c5a0d72c8d
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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