Hydrochloric Acid → HCID 59432811, compound

HRID 1594216Notes

Reaction equation

HRID 1594216 reaction equation
[NH2:1][CH:2]([CH2:8][C:9]([CH3:11])=[CH2:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.CCN(CC)CC.Cl>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][CH:2]([CH2:8][C:9]([CH3:11])=[CH2:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 14163092HCID 14163092, compound

Product 1

HCID 59432811HCID 59432811, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-amino-4-methyl-4-pentenoate (2.84 g, 18.1 mmol, prepared as in Reaction Scheme 19 from (benzhydrylideneamino)acetic acid ethyl ester and 1-bromo-2-methyl-2-propene) in CH2Cl2 (250 mL) was reacted with 4-chlorobenzenesulfonyl chloride (4.20 g, 19.9 mmol) and Et3N (3.78 mL, 27.2 mmol). After 4 h, the resulting mixture was poured into 1 N aqueous HCl (500 mL) and extracted with EtOAc (3×150 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude concentrate was purified using silica gel column chromatography (10:1 to 5:1 gradient, hexanes/EtOAc) to afford 3.04 g (25% yield over 3 steps) of ethyl 2-(4-chlorobenzenesulfonylamino)-4-methyl-4-pentenoate: LCMS (M+Na)+354.2; 1H NMR (400 MHz, CDCl3) 7.77 (d, 2H, J=9.1), 7.46 (d, 2H, J=8.8), 5.07 (d, 1H, J=9.0), 4.84 (s, 1H), 4.73 (s, 1H), 4.05 (m, 1H), 3.95 (q, 2H, J 7.1), 2.40 (m, 2H), 1.66 (s, 3H), 1.13 (t, 3H, J=7.1).

Workup

  1. extractionextracted with EtOAc (3×150 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationThe crude concentrate
  7. customwas purified

Sources & evidence

ORD record
ord-42e8156779714fa1bb1b6311bcd0191b
Source dataset
uspto-grants-2007_11
Patent number
US07300936B2

Reaction notes

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