(2-Bromoethoxy)-tert-butyldimethylsilane → (4S,5S)-5-(4-(2-((tert-Butyldimethylsilyl)oxy)ethoxy)phenyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)oxazolidin-2-one

HRID 929950Notes

Reaction equation

HRID 929950 reaction equation
C([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:10]([O:12]C)=O)=[O:7])(C)(C)C.Br[CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CCCCCCC.CCOC(C)=O>[Si:26]([O:25][CH2:24][CH2:23][O:21][C:18]1[CH:17]=[CH:16][C:15]([C@@H:14]2[O:7][C:6](=[O:5])[NH:8][C@H:9]2[CH2:10][O:12][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[CH:20][CH:19]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 7016055Boc-D-Tyr-OMe

Product 1

HCID 86718532(4S,5S)-5-(4-(2-((tert-Butyldimethylsilyl)oxy)ethoxy)phenyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to the procedure described for intermediate 11 starting with (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate and (2-bromoethoxy)(tert-butyl)dimethylsilane. TLC (heptane/EtOAc 1:1) Rf=0.51; tR=1.764 min (UPLC 1); LC-MS: [M+H] 482; Rt 1.57 min; (LCMS method 1); 1H NMR (400 MHz, CDCl3): 7.31 (d, 2H), 6.96 (d, 2H), 5.26 (br s, 1H), 5.22 (d, 1H), 4.13 (m, 2H), 4.00 (m, 2H), 3.79 (m, 1H), 3.67 (m, 2H), 0.93 (s, 9H), 0.92 (s, 9H), 0.11 (m, 12H).

Sources & evidence

ORD record
ord-42b00ab01c9d459abc389db36a82a2e6
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

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