Sodium hydride → Tert-butyl propyl[5-(tributylstannanyl)-1,3-thiazol-2-yl]carbamate

HRID 513185

Reaction equation

[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([C:14]1[S:18][C:17]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:16][CH:15]=1)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9].[H-].[Na+].I[CH2:30][CH2:31][CH3:32]>CN(C=O)C.O>[CH2:30]([N:19]([C:17]1[S:18][C:14]([Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:10][CH2:11][CH2:12][CH3:13])=[CH:15][N:16]=1)[C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:31][CH3:32]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(N-BOC)-5-(tributylstannyl)thiazole (200 mg, 0.409 mmole) in DMF (2 mL) was added NaH (60% dispersion in mineral oil, 20 mg, 0.500 mmole) at RT. After gas evolution had ceased 1-iodopropane (0.048 mL, 0.490 mmole) was added and the mixture was heated to 60° C. After stirring overnight the mixture was cooled to RT, diluted with H2O, and extracted with EtOAc (3×). The combined organic layers were washed with H2O and brine, dried (MgSO4), filtered, and concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, 0-10% EtOAc/hexanes) gave the title compound (155 mg, 71%) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 7.33 (s, 1 H); 4.11-4.03 (m, 2 H); 1.79-1.69 (m, 1 H); 1.62-1.52 (m, 18 H); 1.38-1.28 (m, 7 H); 1.13-1.05 (m, 7 H); 0.95 (m, 3 H); 0.93-0.84 (m, 9 H).

Workup

additionwas added
temperaturewas cooled to RT
extractionextracted with EtOAc (3×)
washThe combined organic layers were washed with H2O and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d8b3ecc9d1884734a266cf9b3300f758
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102673B2

Linked notes

Loading…