Triethylamine → Carbamic acid, [1-[(methoxymethylamino)carbonyl]-3-pentynyl]-, 1,1-dimethylethyl ester

HRID 342145Notes

Reaction equation

HRID 342145 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]#[C:15][CH3:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][NH:19][O:20][CH3:21].C1C=C2N=NN(O)C2=CC=1.O.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]#[C:15][CH3:16])[C:10]([N:19]([O:20][CH3:21])[CH3:18])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21187433183500-60-9

Product 1

HCID 21258867Carbamic acid, [1-[(methoxymethylamino)carbonyl]-3-pentynyl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Step D (10.58 g, 46.6 mmol), N,O-dimethylhydroxylamine hydrochloride (9.09 g, 93.2 mmol), HOBT hydrate (9.44 g, 69.9 mmol) and triethylamine (13.0 mL, 93.2 mmol) were stirred in dry DMF (150 mL) at 0° C. under nitrogen. EDC hydrochloride (11.5 g, 60.6 mmol) was added, and the reaction was stirred for 3 hours. The solution was partitioned between 2:1 ethyl acetate:hexane and water, washed with water, 10% aq. HCl, sat. NaHCO3 soln and brine, then dried with sodium sulfate. The solvent was removed in vacuo to give the title compound as an orange oil

Workup

  1. customThe solution was partitioned between 2:1 ethyl acetate
  2. washhexane and water, washed with water, 10% aq. HCl, sat. NaHCO3 soln
  3. dry with materialbrine, then dried with sodium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dd1cf2382c774964b6c079a3b8bb66e4
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

Loading…