1,2-Dichloroethane → Tert-butyl (5-(methoxy(methyl)amino)-5-oxopentyl)carbamate

HRID 1837917Notes

Reaction equation

HRID 1837917 reaction equation
[C:1]([NH:8][CH:9]([CH2:13][CH2:14][CH3:15])C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.N([O:19][CH3:20])C.C(Cl)CCl.C1C=CC2N([OH:34])N=NC=2C=1.C[N:36]1[CH2:41]COC[CH2:37]1>CC#N>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH2:13][CH2:14][CH2:15][C:41](=[O:34])[N:36]([O:19][CH3:20])[CH3:37])([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 757711-HydroxybenzotriazoleHCID 3024332-(((Tert-butoxy)carbonyl)amino)pentanoic acid

Product 1

HCID 17958956Tert-butyl (5-(methoxy(methyl)amino)-5-oxopentyl)carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Boc-aminovaleric acid 21-1 (92 mmol) was dissolved in CH3CN (300ml) and then treated with HCl.HN(Me)OMe (10.8 g, 110 mmol), EDC (17.6g, 92 mmol), HOBT (12.4 g, 92 mmol) and NMM (61 mL, 552 mmol). The mixture was stirred for 18 hours and then concentrated. The residue was dissolved in ethyl acetate, washed with H2O, 10% KHSO4, sat. NaHCO3, brine, dried (MgSO4), and concentrated to give amide 21-2 as a brown oil.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with H2O, 10% KHSO4, sat. NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e47b5a7116b546d8ac509724f15efb9a
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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