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

HRID 1956684Notes

Reaction equation

HRID 1956684 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 esterYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Step I (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 (11.10 g, 88 % yield) 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-c6262de9bc24417790a6188a19ba525f
Source dataset
uspto-grants-1998_07
Patent number
US05780492

Reaction notes

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