Ethyl bromoacetate → HCID 70045577, compound

HRID 1198492Notes

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]2[CH2:20][CH2:19][NH:18][C:17]2=[O:21])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:33][C:34]([O:36][CH2:37]C)=[O:35]>C1COCC1>[C:34]([O:36][CH3:37])(=[O:35])[CH3:33].[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]2[CH2:20][CH2:19][NH:18][C:17]2=[O:21])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Conditions

Temperature: -20 °C

Procedure

To a stirred solution of 36a (340 mg, 1.1 mmol) in THF (10 mL) at -78° C. was added NaN(TMS)2 (1.0M in THF, 1.1 mL). After 15 minutes ethyl bromoacetate (250 uL, 2.2 mmol) was added and the reaction mixture to warm to -20° C. After 2 hours the reaction was quenched with HOAc (0.1 mL) and then concentrated. Flash chromatography (silica gel, 50% ethyl acetate/hexanes) gave 37a (380 mg, 90%) as an oil. TLC Rf=0.66 (10% methanol/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 4.22 (q, J=7 Hz, 2H), 4.10 (m, 2H), 4.08 (s, 2H), 3.24 (m, 2H), 2.70 (m, 2H), 2.44 (m, 1H), 2.26 (m, 1H), 2.00-1.65 (m, 4H), 1.48 (s, 9H), 1.50-1.30 (m, 4H), 1.31 (t, J=7 Hz, 3H), 1.12 (m, 2H).

Workup

customAfter 2 hours the reaction was quenched with HOAc (0.1 mL)
concentrationconcentrated

Sources & evidence

ORD record: ord-750cf642abaa403c8383fb5cfa43fe01
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281585

Reaction notes

Loading…