Methanol → HCID 57572489, compound

HRID 1038283Notes

Reaction equation

HRID 1038283 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([N:11]2[CH2:15][CH2:14][S:13][C:12]2=[S:16])=[O:10])=[CH:7][C:6]([C:17]([N:19]2CCSC2=S)=[O:18])=[CH:5][C:4]=1[C:25]([N:27]1[CH2:31][CH2:30][S:29][C:28]1=[S:32])=[O:26].C(N(CC)CC)C.Cl.[CH2:41]([O:43][C:44](=[O:48])[C@H:45]([CH3:47])N)[CH3:42].CO>ClCCl.CN(C=O)C>[CH2:41]([O:43][C:44](=[O:48])[CH2:45][CH2:47][NH:19][C:17](=[O:18])[C:6]1[CH:7]=[C:8]([C:9]([N:11]2[CH2:15][CH2:14][S:13][C:12]2=[S:16])=[O:10])[C:3]([O:2][CH3:1])=[C:4]([C:25]([N:27]2[CH2:31][CH2:30][S:29][C:28]2=[S:32])=[O:26])[CH:5]=1)[CH3:42]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)HCID 57572464HCID 57572464, compound

Product 1

HCID 57572489HCID 57572489, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To slurry of the 2-methoxy-TIAM-trithiazolide 5 (27.1 g, 0.05 mol) and triethylamine (2 mL) in dichloromethane (600 mL), a solution of □-alanine ethyl ester HCl salt (1.1 g, 7 mmol) in DMF (15 mL) and dichloromethane (100 mL) was added dropwise over 36 h. The reaction mixture was applied directly onto a gradient flash silica column (1-3% methanol in dichloromethane). The desired product was obtained as thick, yellow oil. Yield 2.3 g (61% based on the □-alanine ethyl ester HCl salt).

Sources & evidence

ORD record
ord-5c5ff42fc7434cdab4df2bea8fb5cffd
Source dataset
uspto-grants-2013_10
Patent number
US08551453B2

Reaction notes

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