alpha-Chlorohydrin, (+)- → HCID 24936207, compound

HRID 2047319Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([N:21]([CH:23]([CH3:25])[CH3:24])[CH3:22])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:26])[C:4]=1[OH:27])[CH3:2].Cl[CH2:29][C@@H:30]([OH:33])[CH2:31][OH:32]>>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([N:21]([CH:23]([CH3:24])[CH3:25])[CH3:22])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:26])[C:4]=1[O:27][CH2:29][C@@H:30]([OH:33])[CH2:31][OH:32])[CH3:2]

Participants

Reactant 2

HCID 148904alpha-Chlorohydrin, (+)-

HCID 136375861HCID 136375861, compound

Product 1

HCID 24936207HCID 24936207, compound

Procedure

(S)-3-(2-Ethyl-4-{5-[2-(isopropyl-methyl-amino)-6-methyl-pyridin-4-yl]-[1,2,4]oxa-diazol-3-yl}-6-methyl-phenoxy)-propane-1,2-diol is prepared from 2-ethyl-4-{5-[2-(isopropyl-methyl-amino)-6-methyl-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenol and (S)-3-chloro-1,2-propanediol in analogy to Example 3; LC-MS: tR=1.07 min; [M+1]+=441.37; 1H NMR (CDCl3): δ 1.24 (d, J=6.5 Hz, 6H), 1.33 (t, J=7.5 Hz, 3H), 2.05 (t, J=5.1 Hz, 1H), 2.41 (s, 3H), 2.51 (s, 3H), 2.73 (d, J=5.5 Hz, 1H), 2.78 (q, J=7.5 Hz, 2H), 2.97 (s, 3H), 3.81-4.00 (m, 4H), 4.12-4.21 (m, 1H), 4.95-5.05 (m, 1H), 7.06 (s, 1H), 7.13 (s, 1H), 7.88 (s, 1H), 7.89 (s, 1H).

Sources & evidence

ORD record: ord-80254d741c13438caf7f8ea1b592c4d5
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592460B2

Reaction notes

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