4-Methylmorpholine → HCID 68157628, compound

HRID 243000Notes

Reaction equation

HRID 243000 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[NH2:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([O:28][C:29]([NH:31][C@@H:32]([CH3:36])[C:33](O)=[O:34])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([NH:12][C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[NH:20][C:33](=[O:34])[C@@H:32]([NH:31][C:29]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:30])[CH3:36])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 181649HOAtHCID 736104N-carbobenzyloxyalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68157973HCID 68157973, compound

Product 1

HCID 68157628HCID 68157628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(2-amino-5-fluorophenylamino)azetidine-1-carboxylic acid tert-butyl ester (15.5 mmol), (S)-2-benzyloxycarbonylaminopropionic acid (3.81 g, 17.1 mmol), HOAt (2.32 g, 17.1 mmol), 4-methylmorpholine (3.75 mL, 34.1 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3.27 g, 17.1 mmol) in DCM (53 mL) was stirred at RT for 2 h. The reaction mixture was partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with EtOAc (×3) and the combined organic fractions were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow oil (quantitative). LCMS (Method B): RT 3.63 min [M+H]+ 487.3.

Workup

  1. customThe reaction mixture was partitioned between EtOAc
  2. extractionThe aqueous phase was further extracted with EtOAc (×3)
  3. washthe combined organic fractions were washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28a15365816d4bb687a596debf2e2184
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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