tert-Butyl bromoacetate → HCID 70076336, compound

HRID 1737115Notes

Reaction equation

HRID 1737115 reaction equation
C(O[C:6](=[O:26])[CH2:7][C@@H:8]([CH2:20][C:21]1[N:22]=[CH:23][S:24][CH:25]=1)[C:9]([N:11]1[C@@H:15]([CH:16]([CH3:18])C)[CH2:14][O:13]C1=O)=[O:10])(C)(C)C.[CH3:27][N:28]([CH3:41])[C:29](=[O:40])[CH2:30][NH:31][C@H:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:33].BrCC(O[C:47]([CH3:50])([CH3:49])[CH3:48])=O.C[CH2:52][O:53]C(C)=O.[CH3:57][CH2:58][CH2:59][CH2:60][CH2:61]C>>[CH3:41][N:28]([CH3:27])[C:29](=[O:40])[CH2:30][N:31]([C@H:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:33])[C:6](=[O:26])[CH2:7][C@@H:8]([CH2:20][C:21]1[N:22]=[CH:23][S:24][CH:25]=1)[C:9]([NH:11][C@@H:15]([CH2:16][CH:18]1[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1)[C@@H:14]([OH:13])[C@@H:52]([OH:53])[CH2:50][CH:47]([CH3:48])[CH3:49])=[O:10]

Participants

5

Reactant 4

HCID 79177tert-Butyl bromoacetateHCID 21226206Ethyl acetate hexane2×HCID 22861557HCID 22861557, compound2×HCID 28564749HCID 28564749, compound

Product 1

HCID 70076336HCID 70076336, compoundYield 75%

Procedure

3-[4-tert-Butoxy-1,4-dioxo-2(R)-(4-thiazolylmethyl)butyl]-4(S)-(1-methylethyl)-2-oxazolidinone: The product of section (a) of this example (825 mg, 3.07 mmol) was stereoselectively alkylated with tert-butyl 2-bromoacetate according to the procedure described in example 2, section (f) to give a mixture of the desired 3-[4-tert-butoxy-1,4-dioxo-2(R)-(4-thiazolylmethyl)butyl]-4(S)-(1-methylethyl)-2-oxazolidinone (Rf=0.25, eluent: EtOAc-hexane, 1:2) and its corresponding 2(S)-epimer (Rf=0.41, eluent: EtOAc-hexane, 1:2) in a 7:1 ratio, respectively. Flash chromatography (SiO2, eluent: EtOAc-hexane, 1:2) yielded the pure desired compound as a white solid (882 mg, 75%), 1H NMR(CDCl3) δ8.75 (s,1H), 7.14 (s,1H), 4.62-4.5 (m,1H), 4.50-4.40 (m,1H), 4.29-4.20 (m,2H), 3.19 (dd, J=6.4 Hz,14.2 Hz,1H), 3.02 (dd, J=7.5 Hz,14.2 Hz,1H), 2.84 (dd, J=9.8 Hz,16.6 Hz,1H), 2.49 (dd, J=4.7 Hz,16.6 Hz,1H), 1.41 (s,9H), 0.95 (d, J=6.8 Hz,3H), 0.92 (d, J=7.0 Hz,3H).

Workup

  1. customto give

Sources & evidence

ORD record
ord-70f86f582d8641feb86d38934b2326a7
Source dataset
uspto-grants-1996_07
Patent number
US05541163

Reaction notes

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