3-Bromo-2-methyl-1-propene → HCID 86694365, compound

HRID 538934Notes

Reaction equation

HRID 538934 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]([C@@H:19]([CH3:22])[CH:20]=[O:21])[C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.Br[CH2:26][C:27]([CH3:29])=[CH2:28]>>[OH:21][CH:20]([CH2:28][C:27]([CH3:29])=[CH2:26])[CH:19]([N:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:24][CH:23]=1)[C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:22]

Participants

3

Reactant 2

HCID 3577853-Bromo-2-methyl-1-propeneHCID 86694363HCID 86694363, compound

Product 1

HCID 86694365HCID 86694365, compound

Procedure

The title compound was prepared in analogy to the procedure described for step 23.7 from (S)-benzyl 4-methoxybenzyl(1-oxopropan-2-yl)carbamate and 3-bromo-2-methylprop-1-ene to afford the title compound as a 3:1 mixture of (2S,3R)- and (2S,3S)-diastereomer: tR=1.322 min (major isomer) and 1.329 min (minor isomer) (UPLC 1); tR=1.23 min (major isomer) and 1.24 min (minor isomer) (LC-MS 3); ESI-MS: 384 [M+H]+ (LC-MS 3).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-3566179c237445c3b6b9f01e4ce553fd
Source dataset
uspto-grants-2014_10
Patent number
US08865894B2

Reaction notes

Loading…