Triethylamine → HCID 59294388, compound

HRID 1958702Notes

Reaction equation

HRID 1958702 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C(N(CC)CC)C.[Br:27][C:28]1[S:32][C:31]([S:33](Cl)(=[O:35])=[O:34])=[CH:30][CH:29]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:27][C:28]1[S:32][C:31]([S:33]([NH:3][C@@H:4]([CH2:16][N:17]([CH3:18])[CH3:19])[CH2:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])(=[O:35])=[O:34])=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochloride

Product 1

HCID 59294388HCID 59294388, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochloride (1 g, 3.2 mmol), triethylamine (1.3 mL, 9.6 mmol) and DMAP (20 mg, 0.16 mmol) in anhydrous CH2Cl2 (25 mL) was added 5-bromothiophene-2-sulfonyl chloride (2.5 g, 9.6 mmol). Methylene chloride (200 mL) was added and the solution was washed with dilute NaOH (10 mL), water (10 mL), dried over MgSO4 and concentrated to dryness. The residue was purified by silica gel chromatography (95:5 CH2Cl2/MeOH) to give the title compound as a yellow solid (650 mg, 44%). 1H NMR (400 MHz, CDCl3) δ 7.44 (d, 1H, J=3.8 Hz), 7.41-7.27 (m, 5H), 7.04 (d, 1H, J=3.8 Hz), 5.14-5.07 (m, 2H), 3.87-8.83 (m, 1H), 2.92-2.89 (m, 1H), 2.83-2.78 (m, 1H), 2.69-2.64 (m, 1H), 2.60-2.54 (m, 1H), 2.43 (s, 6H); MS ESI 461.3 [M+H]+, calcd for [C17H21BrN2O4S2]+ 461.00.

Workup

  1. washthe solution was washed with dilute NaOH (10 mL), water (10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by silica gel chromatography (95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-97a79b81638743438853f524676c745d
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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