Water → HCID 22219880, compound

HRID 1794060Notes

Reaction equation

HRID 1794060 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][SH:16])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][N:34]([C:37](Cl)=[O:38])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].O>C1COCC1.CN(C1C=CN=CC=1)C>[C:24]([O:28][C:29]([N:31]1[CH2:32][CH2:33][N:34]([C:37](=[O:38])[S:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:14][CH:13]=2)[CH2:35][CH2:36]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylateHCID 222200084-(Tert-butyldimethylsilyloxy)-benzenemethanethiol

Product 1

HCID 22219880HCID 22219880, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

to a stirred solution of 4-(tert-butyldimethylsilyloxy)-benzenemethanethiol (10.5 g, 41 mmol) and triethylamine (69 mmol, 9.6 mL) in THF (500 mL) at 0° C. was added 4-tert-butoxycarbonyl-1-chlorocarbonylpiperazine (8.56 g, 34 mmol) and DMAP (6.9 mmol, 0.84 g). The reaction mixture was warmed to 50° C. and stirred for 3 h then poured into water (500 mL) and extracted with EtOAc (2×250 mL). The combined organic extracts were washed with water (250 mL) then brine (500 mL), then dried (MgSO4) and concentrated to reveal a brown oil. Chromatography [SiO2: 90/10, hexane/EtOAc)] gave the product as a yellow oil which crystallised on standing (13.4 g, 85%): m.p. 53–54° C. 1H-NMR (400 MHz, CDCl3): 0.18 (6H, s), 0.96 (9H, s), 1.46 (9H, s), 3.42–3.51 (8H, m), 4.12 (2H, s), 6.75 (2H, d, J=8.5 Hz) and 7.18 (2H, d, J=8.5 Hz).

Workup

  1. extractionextracted with EtOAc (2×250 mL)
  2. washThe combined organic extracts were washed with water (250 mL)
  3. dry with materialbrine (500 mL), then dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c37cf62eb54c4940b45080b59225802c
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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