Triethylamine → HCID 68157546, compound

HRID 242826Notes

Reaction equation

HRID 242826 reaction equation
CCN(CC)CC.[O:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:16]([NH2:21])=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1.[C:22]([O:26][C:27]([NH:29][C@@H:30]([CH3:34])[C:31](O)=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].C1C=NC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:22]([O:26][C:27](=[O:28])[NH:29][C@H:30]([C:31](=[O:32])[NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][CH:11]1[CH2:10][CH2:9][O:8][CH2:13][CH2:12]1)[CH3:34])([CH3:23])([CH3:24])[CH3:25]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 43609747HCID 43609747, compound

Product 1

HCID 68157546HCID 68157546, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et3N (2.6 mL, 18.9 mmol) was added to a stirred mixture of N-(tetrahydropyran-4-yl)benzene-1,2-diamine (1.21 g, 6.29 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (1.31 g, 6.92 mmol), HOAt (0.94 g, 6.92 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.33 g, 6.92 mmol) in anhydrous DCM (30 mL) at 0° C. under a nitrogen atmosphere. Stirring was continued for 10 min at 0° C. then the mixture was slowly warmed to RT and stirred at RT for 4 h. The reaction mixture was partitioned between DCM and a saturated solution of NaHCO3. The aqueous phase was further extracted with DCM and the combined organic layers were then washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% 2M NH3/MeOH in DCM) affording {(S)-1-[2-(Tetrahydropyran-4-ylamino)phenylcarbamoyl]ethyl}carbamic acid tertbutyl ester as a white solid (1.91 g, 83%). LCMS: RT 2.78 min [M+H-tBu]+ 308.1.

Workup

  1. stirringstirred at RT for 4 h
  2. customThe reaction mixture was partitioned between DCM
  3. extractionThe aqueous phase was further extracted with DCM
  4. washthe combined organic layers were then washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-9b8173915d5140f7876e18b2a76d0300
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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