Thiophenol → HCID 53778325, compound

HRID 2185518Notes

Reaction equation

HRID 2185518 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C@@H:5]1[CH2:9][CH:8]([CH2:10][CH2:11][CH2:12][N:13]=[N+]=[N-])[CH2:7][N:6]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.C1(S)C=CC=CC=1.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:23])[C@@H:5]1[CH2:9][CH:8]([CH2:10][CH2:11][CH2:12][NH2:13])[CH2:7][N:6]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:2]

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 8471TriethylamineHCID 24287Tin tetrachlorideHCID 54242216HCID 54242216, compound

Product 1

HCID 53778325HCID 53778325, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

N-(tert-butoxycarbonyl)-4-(3-azidopropyl)-L-proline ethyl ester (1.17 g, 3.58 mmol) was dissolved in anhydrous tetrahydrofuran (40 mL) and dry tin chloride (1.01 g, 1.5 eq.), thiophenol (2.21 mL, 6 eq.) and triethylamine (2.24 mL, 4.5 eq.) were added. The reaction mixture was stirred at 25° C. for Ihour, poured into ethyl acetate, washed with 1 N HCl, 1 N NaOH, brine, dried (Na2SO4) and concentrated. The residue (0.96 g, 90%) was used crude in the next step: 1H NMR (400 MHz, CDCl3, 7:3 mixture of diastereomers) δ 1.29 (m, 3H), 1.40-1.56 (m, 9H), 1.84 (m, 1H), 2.10 (m, 1H), 2.39 (m, 1H), 2.42 (m, 1H), 2.72 (m, 2H), 2.99 (m, 2H), 3.76 (m, 2H) 4.18-4.38 (m, 4H).

Workup

  1. washwashed with 1 N HCl, 1 N NaOH, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cf7732167ee34b8d8fc28957438f5386
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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