Triethylamine → HCID 67350582, compound

HRID 1672822Notes

Reaction equation

HRID 1672822 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20](O)=[O:21])[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:26]=1.Cl.[CH3:28][O:29][C:30](=[O:35])[C@H:31]([CH2:33]O)[NH2:32].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:20]4[O:21][CH2:33][C@@H:31]([C:30]([O:29][CH3:28])=[O:35])[N:32]=4)[CH:23]=[CH:24][CH:25]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:26]=1

Participants

11

Reactant 7

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 757711-HydroxybenzotriazoleHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67350552HCID 67350552, compound

Product 1

HCID 67350582HCID 67350582, compoundYield 75.1%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic acid (150 mg, 0.405 mmol) obtained in Step 1 of Example 56 was dissolved in dichloromethane (5 mL), and the mixture was stirred for 4 hours after adding L-serine methyl ester hydrochloride (95.0 mg, 0.607 mmol), triethylamine (0.0850 mL, 0.607 mmol), 1-ethyl-3-(3dimethylaminopropyl)carbodiimide hydrochloride (93.0 mg, 0.486 mmol), and 1-hydroxybenzotriazole.monohydrate (62.0 mg, 0.405 mol). The mixture was diluted with chloroform and washed with a saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in THF (5 mL), and the mixture was stirred at room temperature for 30 minutes after adding triphenylphosphine (212 mg, 0.810 mmol) and a 40% toluene solution of diethyl azodicarboxylate (0.367 mL, 0.810 mmol). The mixture was concentrated, and the resulting residue was purified by silica gel column chromatography to give methyl (S)-2-{3-[(S)-9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl]phenyl}-4,5-dihydro-1,3-oxazole-4-carboxylate (138 mg, 75%).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in THF (5 mL)
  5. stirringthe mixture was stirred at room temperature for 30 minutes
  6. concentrationThe mixture was concentrated
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e12a35ee737043b0a35ca183abf76e6c
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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