tert-Butyl bromoacetate → HCID 68853462, compound

HRID 28437Notes

Reaction equation

HRID 28437 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. m.p.: 83-85° C.

Sources & evidence

ORD record
ord-74323a26148845b5be5e96189efc452f
Source dataset
uspto-grants-2008_09
Patent number
US07419981B2

Reaction notes

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