Hydrochloric Acid → (Rs)-n-methoxy-n-methyl-2-(4,4-dimethyl-thiochroman-6-yl)-heptanoic amide

HRID 394934Notes

Reaction equation

HRID 394934 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:13](O)=[O:14])[CH:10]=2)[S:5][CH2:4][CH2:3]1.Cl.C([N:26]([CH:29](C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.CN([CH:47]=[O:48])C>C(Cl)Cl>[CH3:47][O:48][N:26]([CH3:29])[C:13](=[O:14])[CH:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[S:5][CH2:4][CH2:3][C:2]2([CH3:21])[CH3:1])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18177798(RS)-2-(4,4-dimethyl-thiochroman-6-yl)-heptanoic acid

Product 1

HCID 87949148(Rs)-n-methoxy-n-methyl-2-(4,4-dimethyl-thiochroman-6-yl)-heptanoic amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.44 g of (RS)-2-(4,4-dimethyl-thiochroman-6-yl)-heptanoic acid was dissolved in a mixture of 2.1 ml DMF/4.2 ml of methylene chloride, and 1.35 g of MeO(Me)NH.HCl was added followed by 2.47 ml of diisopropylethylamine and 0.53 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. The reaction mixture was stirred at room temperature for 4 hours, then the volatiles were removed in vacuo. The residue was taken up in 100 ml ethyl acetate and washed with one portion of 50 ml of water, one portion of 50 ml of 1N hydrochloric acid, one portion of 50 ml of saturated aqueous sodium bicarbonate solution and one portion of 50 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated in vacuo, giving 0.49 g of a yellow oil. The crude product was used without purification. 1H NMR (CDCl3): 7.27 (d, J=1.8 Hz, 1H), 7.02 (d, J=8.1 Hz, 1H), 6.95 (dd, J=8.1, 1.8 Hz, 1H), 3.48 (s, 3H), 3.35-3.20 (m, 1H), 3.15 (s, 3H), 3.05-2.95 (m, 2H), 2.00-1.90 (m, 2H), 1.75-1.55 (m, 2H), 1.32 (s, 3H), 1.26 (s, 3H), 1.35-1.20 (m, 6H), 0.85 (t, J=6.9 Hz, 3H).

Workup

  1. customthe volatiles were removed in vacuo
  2. washwashed with one portion of 50 ml of water, one portion of 50 ml of 1N hydrochloric acid, one portion of 50 ml of saturated aqueous sodium bicarbonate solution and one portion of 50 ml of saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d062af2129184c0288c5ac14ab0c185c
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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