Triethylamine → (S)-2-({1-[2-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazol-7-yl]-methanoyl}-amino)-3-phenylpropionic acid

HRID 25322Notes

Reaction equation

HRID 25322 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[NH:16][C:17]4[CH:27]=[CH:26][C:25]5[C:20](=[C:21]([OH:31])[CH:22]=[C:23]([C:28](O)=[O:29])[CH:24]=5)[C:18]=4[N:19]=3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].Cl.C([O:37][C:38](=[O:48])[C@H:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH2:40])(C)(C)C.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C=O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[NH:16][C:17]4[CH:27]=[CH:26][C:25]5[C:20](=[C:21]([OH:31])[CH:22]=[C:23]([C:28]([NH:40][C@@H:39]([CH2:41][C:42]6[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=6)[C:38]([OH:37])=[O:48])=[O:29])[CH:24]=5)[C:18]=4[N:19]=3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)HCID 22566594HCID 22566594, compound

Product 1

HCID 69548299(S)-2-({1-[2-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazol-7-yl]-methanoyl}-amino)-3-phenylpropionic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To the 2-(3′,4′-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-carboxylic acid (0.05 g, 0.1 mmol) in DMF (0.5 mL) at room temperature was added phenylalanine tert butyl ester hydrochloride (0.11 mmol). A cocktail solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.021 g, 0.11 mmol), triethylamine (0.3 mmol) in DMF (0.5 mL) was added and the reaction was agitated at room temperature for 18 hours. 1 ml water was added to the reaction mixture resulting in the formation of a tan precipitate. the mixture was filtered and allowed to dry. The solid mass was transferred into vial and dissolved in 90% trifluoroacetic acid (1 mL). The solutions were agitated for 6 hrs then concentrated under reduced pressure. The residures were taked up in DMSO and subjected to Gilson HPLC purification. The title compound was abtained as solid.(0.006 g, 10%). MS(ES) m/z 556 [M+H].

Workup

  1. customresulting in the formation of a tan precipitate
  2. filtrationthe mixture was filtered
  3. customto dry
  4. dissolutiondissolved in 90% trifluoroacetic acid (1 mL)
  5. stirringThe solutions were agitated for 6 hrs
  6. concentrationthen concentrated under reduced pressure
  7. customsubjected to Gilson HPLC purification

Sources & evidence

ORD record
ord-6cda9d8a4f6b45b08cc6aac2eabb2b79
Source dataset
uspto-grants-2005_02
Patent number
US06858630B2

Reaction notes

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