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

HRID 379260Notes

Reaction equation

HRID 379260 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-f5ca280c51484b00b55a5468ad3e1c2e
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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