Dichloromethane → HCID 10234075, compound

HRID 488666Notes

Reaction equation

HRID 488666 reaction equation
[C:1]([NH:4][C@H:5]([C:50]([NH:52][CH2:53][CH2:54][CH2:55][CH2:56][O:57][C:58]1[C:63]([C:64]([O:66][CH3:67])=[O:65])=[C:62]([OH:68])[C:61]([Br:69])=[CH:60][CH:59]=1)=[O:51])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([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:14](=[O:25])[C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[C:9]([CH2:48][CH3:49])[CH:8]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.C(Cl)Cl.[OH-].[Na+]>C1COCC1.CO>[C:1]([NH:4][C@H:5]([C:50]([NH:52][CH2:53][CH2:54][CH2:55][CH2:56][O:57][C:58]1[C:63]([C:64]([O:66][CH3:67])=[O:65])=[C:62]([OH:68])[C:61]([Br:69])=[CH:60][CH:59]=1)=[O:51])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([C:14]([C:15]([OH:17])=[O:16])=[O:25])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([OH:34])=[O:33])=[C:9]([CH2:48][CH3:49])[CH:8]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86585328HCID 86585328, compound

Product 1

HCID 10234075HCID 10234075, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-{4-[(N-acetyl-4-{{2-[(benzhydryloxy)carbonyl]phenyl}[(benzyloxy)(oxo)acetyl]amino}-3-ethylphenylalanyl)amino]butoxy}-3-bromo-2-hydroxybenzoate was treated with trifluoroacetic acid (500 μL)/methylene chloride (500 μL) at ambient temperature for 4 hours, concentrated under reduced pressure and co-evaporated with acetonitrile (2×10 mL). The residue was taken up in 1N NaOH (3 eq.)/methanol (250 μL)/THF (250 μL), stirred for 3 hours and concentrated under reduced pressure to provide the titled compound. MS (ESI (+)) m/e 742, 743 (M+H)+; 1H NMR (500 MHz, DMSO-d6) 8.08-7.92 (m, 2H), 7.45-6.94 (m, 7H), 6.64 (d, 2H), 4.43-4.38 (m, 1H), 3.90-3.86 (m, 2H), 3.78 (s, 3H), 3.10-3.05 (m, 2H), 2.90-2.85 (m, 1H), 2.75-2.62(m, 3H), 1.76(s, 3H), 1.64-1.58 (m, 2H), 1.52-1.45 (m, 2H), 1.18 (t, 3H).

Workup

  1. concentrationconcentrated under reduced pressure and co-evaporated with acetonitrile (2×10 mL)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c44a5d7073b94c0ebcc82b8b9b5947f9
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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