Allyl Alcohol → HCID 18322378, compound

HRID 1698890Notes

Reaction equation

HRID 1698890 reaction equation
[C:1]([NH:8][C:9]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[S:11][C:10]=1[C:18]([OH:20])=[O:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:21](O)[CH:22]=[CH2:23].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([NH:8][C:9]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[S:11][C:10]=1[C:18]([O:20][CH2:23][CH:22]=[CH2:21])=[O:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 7858Allyl AlcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2757206HCID 2757206, compound

Product 1

HCID 18322378HCID 18322378, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3-(N-carbo-tert-butoxyamino)-5-tert-butylthiophene-2-carboxylic acid (0.20 g, 0.67 mmol), allyl alcohol (0.042 g, 0.73 mmol, 1.1 equiv) and DMAP (0.008 g, 0.07 mmol, 10 mol %) in CH2Cl2 (2 mL) was added EDCI.HCl (0.14 g, 0.73 mmol, 1.1 equiv). The CH2Cl2 mixture was stirred at room temp. for 3 d, diluted with CH2Cl2, washed with a 1N HCl solution (5 mL) and a saturated NaHCO3 solution (5 mL), dried (Na2SO4), and concentrated under reduced pressure to afford allyl 3-(N-carbo-tert-butoxyamino)-5-tert-butylthiophene-2-carboxylate (0.15 g, 65%) as a colorless oil: TLC (50% CH2Cl2/hexane) Rf0.63; 1H NMR (CDCl3) δ1.37 (s, 9H), 1.50 (s, 9H), 4.74 (ddd, J=5.5, 1.5, 1.5 Hz, 2H), 5.26 (dd, J=10.3, 1.5 Hz, 1H), 5.37 (dd, J=17.3, 1.5 Hz, 1H), 5.87-5.98 (m, 1H), 7.68, 9.35; 13C NMR (CDCl3) δ28.2 (3C), 31.8 (3C), 35.2, 64.9, 80.8, 104.9, 116.4, 118.1, 132.0, 145.6, 152.1, 164.0, 164.4

Workup

  1. washwashed with a 1N HCl solution (5 mL)
  2. dry with materiala saturated NaHCO3 solution (5 mL), dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2618625a33da4f3597ff8398c83c008a
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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