Sodium Lactate, L- → (S)-2-Hydroxy-1-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-9-yl]-azetidin-1-yl}-propan-1-one

HRID 1849286Notes

Reaction equation

HRID 1849286 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:6]=[CH:7][C:8]3[O:17][CH2:16][CH2:15][C:14]4[S:13][C:12]([C:18]5[N:19]([CH:23]([CH3:25])[CH3:24])[N:20]=[CH:21][N:22]=5)=[N:11][C:10]=4[C:9]=3[CH:26]=2)[CH2:2]1.[C:27]([O-])(=[O:31])[C@H:28]([CH3:30])[OH:29].[Na+]>CN(C=O)C>[OH:29][C@@H:28]([CH3:30])[C:27]([N:1]1[CH2:4][CH:3]([C:5]2[CH:6]=[CH:7][C:8]3[O:17][CH2:16][CH2:15][C:14]4[S:13][C:12]([C:18]5[N:19]([CH:23]([CH3:24])[CH3:25])[N:20]=[CH:21][N:22]=5)=[N:11][C:10]=4[C:9]=3[CH:26]=2)[CH2:2]1)=[O:31]

Participants

4

Reactant 2

HCID 23664767Sodium Lactate, L-HCID 670505299-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Product 1

HCID 58203784(S)-2-Hydroxy-1-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-9-yl]-azetidin-1-yl}-propan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure for 318, 9-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene and sodium L-lactate were reacted in DMF to give 359. LCMS: RT=10.69 min, [M+H]+=440. 1H NMR δ (ppm) (CDCl3): 8.36 (1 H, s), 7.90 (1 H, s), 7.20-7.11 (1 H, m), 7.09-7.01 (1 H, m), 5.84-5.75 (1 H, m), 4.62-4.30 (4 H, m), 4.26-4.07 (3 H, m), 3.98-3.87 (1 H, m), 3.43-3.35 (2 H, m), 1.61 (6 H, d, J=6.65 Hz), 1.32 (3 H, dd, J=10.70, 6.64 Hz). 1 Exchangeable not observed

Sources & evidence

ORD record
ord-8173d01bad31461cb9e4c5474bda46c9
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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