(3-Bromopropoxy)(tert-butyl)dimethylsilane → (4S,5S)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-(4-(3-((tert-butyldimethylsilyl)oxy)propoxy)phenyl)oxazolidin-2-one

HRID 929951Notes

Reaction equation

HRID 929951 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][CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>CCCCCCC.CCOC(C)=O>[Si:27]([O:12][CH2:10][C@H:9]1[C@H:14]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:23][CH2:24][CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[CH:19][CH:20]=2)[O:7][C:6](=[O:5])[NH:8]1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 7016055Boc-D-Tyr-OMe

Product 1

HCID 86718533(4S,5S)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-(4-(3-((tert-butyldimethylsilyl)oxy)propoxy)phenyl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to the procedure described for intermediate 12 starting with (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate and (3-bromopropoxy)(tert-butyl)dimethylsilane. TLC (heptane/EtOAc 1:1) Rf=0.49; tR=1.832 min (UPLC 1); LC-MS: [M+H] 496; Rt 1.62 min (LC-MS method 1); 1H NMR (400 MHz, CDCl3): 7.30 (d, 2H), 6.95 (d, 2H), 5.27 (br s, 1H), 5.22 (d, 1H), 4.13 (dd, 2H), 4.00 (m, 2H), 3.80 (m, 3H), 3.74 (m, 2H), 2.01 (m, 2H), 0.93 (s, 9H), 0.91 (s, 9H), 0.10 (s, 6H), 0.06 (s, 6H).

Sources & evidence

ORD record
ord-55a384e1c1e3485a9922c84cbb31cb21
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

Loading…