HCID 10806434, compound → HCID 10564245, compound

HRID 377207Notes

Reaction equation

HRID 377207 reaction equation
[CH3:1][N:2]1[C@@H:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10](I)[CH:9]=2)[CH2:5][O:4][C:3]1=[O:16].C([Si](CC)(CC)[CH:20]([OH:31])[CH2:21][C:22]#[C:23][Si](CC)(CC)CC)C>CS(C)=O>[CH3:1][N:2]1[C@@H:6]([CH2:7][C:8]2[CH:9]=[C:10]3[C:11](=[CH:12][CH:13]=2)[NH:14][CH:23]=[C:22]3[CH2:21][CH2:20][OH:31])[CH2:5][O:4][C:3]1=[O:16]

Participants

4

Reactant 2

HCID 10806434HCID 10806434, compoundHCID 19358398HCID 19358398, compound

Product 1

HCID 10564245HCID 10564245, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared from (S)-3-methyl-4-(3-iodo-4-aminobenzyl)-1,3-oxazolidin-2-one and 1,4-bis-triethylsilyl-3-butyn-1-ol as described for Intermediate 2, δ (360 MHz, D6 -DMSO) 2.72-2.84 (6H, m, CH of CH2, CH2 and N--Me), 3.13 (1H, dd, J=3.8 and 13.5Hz, CH of CH2), 3.61-3.67 (2H, m, CH2), 3.94-4.02 (2H, m, CH2), 4.11-4.17 (1H, m, CH), 4.58 (1H, t, J=5.3Hz, OH), 6.93 (1H, dd, J=1.5 and 8.3Hz, Ar--H), 7.10 (1H, d. J=1.5Hz, Ar--H), 7.26 (1H, d, J=8.3Hz, Ar--H), 7.38 (1H, s, Ar--H), 10.72 (1H, s, NH).

Sources & evidence

ORD record
ord-ad335967a52644b7a22bacd2f1bd6950
Source dataset
uspto-grants-2000_02
Patent number
US06025374

Reaction notes

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