tert-Butyl bromoacetate → HCID 68853462, compound

HRID 1829836Notes

Reaction equation

HRID 1829836 reaction equation
[CH3:1][C:2]([CH3:23])([CH2:20][CH2:21][CH3:22])[CH2:3][CH2:4][C:5]([N:7]1[CH:11]([CH3:12])[CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][C:8]1=[O:19])=[O:6].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:34]([O:38][C:39](=[O:42])[CH2:40]Br)([CH3:37])([CH3:36])[CH3:35]>>[C:34]([O:38][C:39](=[O:42])[CH2:40][C@@H:4]([C:5]([N:7]1[C@@H:11]([CH3:12])[C@@H:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:9][C:8]1=[O:19])=[O:6])[CH2:3][C:2]([CH3:1])([CH3:23])[CH2:20][CH2:21][CH3:22])([CH3:37])([CH3:36])[CH3:35]

Participants

4

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 21943473HCID 21943473, compound

Product 1

HCID 68853462HCID 68853462, compoundYield 49.3%

Procedure

According to example 1, 5.07 g (16 mmol) of 3-(4,4-dimethyl-heptanoyl)-4-methyl-5-phenyl-oxazolidin-2-one, 18 mL (1N, 18 mmol) of NaHMDS solution and 4.72 mL (32 mmol) of bromo-acetic acid tert-butyl ester gave 3.40 g (49.3%) of the title compound as a crystalline solid. 1HNMR (400 MHz; CDCl3): 0.85–0.89 (m, 12H), 1.18–1.32 (m, 6H), 1.41 (s, 9H), 1.88 (dd, 1H, J=6 Hz, 8.4 Hz), 2.41 (dd, 1H, J=6 Hz, 16 Hz), 2.62 (dd, 1H, J=8.4 Hz, 16 Hz), 4.30–4.40 (m, 1H), 4.72 (m, 1H), 5.62 (d, 1H, J=7 Hz), 7.30–7.40 (m, 5H). m.p.: 83–85° C.

Sources & evidence

ORD record
ord-a814bc8151ca4cdf8a5cf35b90642cc1
Source dataset
uspto-grants-2006_06
Patent number
US07064147B2

Reaction notes

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